Organometallic compound and organic light-emitting device including the same

ABSTRACT

An organic light-emitting device includes an organometallic compound represented by M 1 (L 1 ) n1 (L 2 ) n2 , wherein L 1  is a ligand represented by Formula 1-1: 
     
       
         
         
             
             
         
       
     
     In Formula 1-1, *1 to *4 indicate a binding site to M 1 , and Z 11  and Z 12  are respectively boron (B) and nitrogen (N), or N and B. When M 1  binds to an α-position of the B or N atom, metal-ligand charge transfer in the complex may be improved. An OLED including the organometallic compound may have a long lifespan and improved luminescent efficiency and colorimetric purity.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2018-0146771, filed on Nov. 23, 2018, in the KoreanIntellectual Property Office, the entire content of which isincorporated herein by reference.

BACKGROUND 1. Field

One or more aspects of example embodiments of the present disclosurerelate to an organometallic compound and an organic light-emittingdevice including the same.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emitting devices thatmay have wide viewing angles, high contrast ratios, and/or shortresponse times. In addition, OLEDs may exhibit high luminance, drivingvoltage, and/or response speed characteristics, and may producefull-color images.

An example OLED includes a first electrode on a substrate, and mayinclude a hole transport region, an emission layer, an electrontransport region, and a second electrode sequentially stacked on thefirst electrode. Holes provided by the first electrode may move towardthe emission layer through the hole transport region, and electronsprovided by the second electrode may move toward the emission layerthrough the electron transport region. Carriers (such as holes andelectrons) may recombine in the emission layer to produce excitons.These excitons may transition from an excited state to the ground stateto thereby generate light.

SUMMARY

One or more aspects of example embodiments of the present disclosure aredirected toward an organometallic compound and an organic light-emittingdevice including the same.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented embodiments.

One or more example embodiments of the present disclosure provide anorganometallic compound represented by Formula 1:

wherein, in Formulae 1 and 1-1,

M₁ may be selected from a first-row transition metal, a second-rowtransition metal, and a third-row transition metal,

L₁ may be a ligand represented by Formula 1-1,

L₂ may be selected from a monodentate ligand and a bidentate ligand,

n1 may be 1,

n2 may be selected from 0, 1, and 2,

A₁₁ to A₁₆ may each independently be selected from a C₅-C₆₀ carbocyclicgroup and a C₁-C₆₀ heterocyclic group,

X₁₁ to X₁₈ may each independently be selected from nitrogen (N) andcarbon (C),

Y₁₁ to Y₁₄ may each independently be selected from N, C, oxygen (O), andsulfur (S),

i) Z₁₁ may be boron (B), and Z₁₂ may be N; or ii) Z₁₁ may be N, and Z₁₂may be B,

T₁₁ to T₁₄ may each independently be selected from a single bond,*—O—*′, *—S—*′, *—N(R₁₇)—*′, and *—C(R₁₇)(R₁₈)—*′,

L₁₁ to L₁₃ may each independently be selected from a single bond,*—O—*′, *—S—*′, *—C(R₁₉)(R₂₀)—*′, *—C(R₁₉)═*′, *═C(R₁₉)—*′,*—C(R₁₉)═C(R₂₀)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R₁₉)—*′,*—N(R₁₉)—*′, *—P(R₁₉)—*′, *—Si(R₁₉)(R₂₀)—*′, *—P(R₁₉)(R₂₀)—*′, and*—Ge(R₁₉)(R₂₀)—′,

a11 to a13 may each independently be selected from 0, 1, 2, and 3,provided that at least two selected from a11 to a13 are selected from 1,2, and 3,

when a11 is 0, A₁₁ and A₁₃ may not be linked to each other; when a12 is0, A₁₂ and A₁₄ may not be linked to each other; and when a13 is 0, A₁₁and A₁₂ may not be linked to each other,

R₁₁ to R₂₀ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazino group, a hydrazono group, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedC₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —N(Q₁)(Q₂), —P(Q₁)(Q₂), —C(═O)(Q₁),—S(═O)(Q₁), —S(═O)₂(Q₁), —P(═O)(Q₁)(Q₂), and —P(═S)(Q₁)(Q₂),

at least two adjacent groups selected from R₁₁ to R₂₀ may optionally bebound to form a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

b11 to b16 may each independently be selected from 1, 2, 3, 4, 5, 6, 7,and 8,

Q₁ to Q₃ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀ alkylgroup, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxygroup, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthiogroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group,

*1 to *4 may each independently indicate a binding site to M₁, and

* and *′ each indicate a binding site to an adjacent atom.

One or more example embodiments of the present disclosure provide anorganic light-emitting device including: a first electrode; a secondelectrode; and an organic layer between the first electrode and thesecond electrode, wherein the organic layer may include an emissionlayer and the organometallic compound represented by Formula 1.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects of example embodiments of the presentdisclosure will become apparent and more readily appreciated from thefollowing description, taken in conjunction with the accompanyingdrawings, in which:

FIG. 1 illustrates a schematic cross-sectional view of an organiclight-emitting device according to embodiments of the presentdisclosure;

FIG. 2 illustrates a schematic cross-sectional view of an organiclight-emitting device according to embodiments of the presentdisclosure;

FIG. 3 illustrates a schematic cross-sectional view of an organiclight-emitting device according to embodiments of the presentdisclosure; and

FIG. 4 illustrates a schematic cross-sectional view of an organiclight-emitting device according to embodiments of the presentdisclosure.

DETAILED DESCRIPTION

Reference will now be made in more detail to embodiments, examples ofwhich are illustrated in the accompanying drawings, wherein likereference numerals refer to like elements throughout and duplicativedescriptions thereof may not be provided. In this regard, the presentembodiments may have different forms and should not be construed asbeing limited to the descriptions set forth herein. Accordingly, theembodiments are merely described below, by referring to the drawings, toexplain aspects of the present description. As used herein, the term“and/or” includes any and all combinations of one or more of theassociated listed items. Expressions such as “at least one of”, “oneof”, and “selected from”, when preceding a list of elements, modify theentire list of elements and do not modify the individual elements of thelist. Further, the use of “may” when describing embodiments of thepresent disclosure refers to “one or more embodiments of the presentdisclosure.”

As the present disclosure allows for various changes and numerousembodiments, selected embodiments will be illustrated in the drawingsand described in more detail in the written description. Effects,features, and methods of achieving the present disclosure will beobvious by referring to example embodiments of the present disclosurewith reference to the attached drawings. The present disclosure may,however, be embodied in many different forms and should not be construedas being limited to the embodiments set forth herein.

In the embodiments described in the present specification, an expressionused in the singular encompasses the expression of the plural and viceversa, unless explicitly stated, and/or the alternate form has a clearlydifferent meaning in context.

In the present specification, it is to be understood that terms such as“including,” “having,” and “comprising” are intended to indicate theexistence of the features or components disclosed in the specification,and are not intended to preclude the possibility that one or more otherfeatures or components may exist and/or may be added.

It will be understood that when a layer, region, or component isreferred to as being “on”, “over”, or “onto” another layer, region, orcomponent, it may be directly or indirectly formed over the other layer,region, or component. In some embodiments, for example, interveninglayers, regions, or components may be present. In contrast, when anelement is referred to as being “directly on” another element, nointervening elements are present.

The sizes of components in the drawings (e.g., the thicknesses oflayers, films, panels, regions, etc.) may be exaggerated for clarity andconvenience of explanation. In other words, since sizes and thicknessesof components in the drawings are arbitrarily illustrated forconvenience of explanation, the following embodiments are not limitedthereto.

An organometallic compound may be represented by Formula 1:

M₁(L₁)_(n1)(L₂)_(n2),  Formula 1

wherein, in Formula 1, M₁ may be selected from a first-row transitionmetal, a second-row transition metal, and a third-row transition metal.

For example, in Formula 1, M₁ may be selected from platinum (Pt),palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh),iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium(Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm), butembodiments of the present disclosure are not limited thereto.

In some embodiments, in Formula 1, M₁ may be selected from Pt, Pd, Cu,Ag, Au, Rh, Ir, Ru, and Os, but embodiments of the present disclosureare not limited thereto.

In some embodiments, in Formula 1, M₁ may be selected from Pt and Pd,but embodiments of the present disclosure are not limited thereto.

In Formula 1, L₁ may be a ligand represented by Formula 1-1:

In Formula 1-1, A₁₁ to A₁₆ may each independently be selected from aC₅-C₆₀ carbocyclic group and a C₁-C₆₀ heterocyclic group.

In some embodiments, in Formula 1-1, A₁ and A₁₂ may each independentlybe selected from a C₅-C₆₀ carbocyclic group and a C₁-C₆₀ heterocyclicgroup, and

A₁₃ to A₁₆ may each independently be selected from a C₅-C₆₀ carbocyclicgroup, but embodiments of the present disclosure are not limitedthereto.

In some embodiments, in Formula 1-1, A₁ to A₁₆ may each independently beselected from a benzene group, a naphthalene group, an anthracene group,a phenanthrene group, a phenalene group, a triphenylene group, a pyrenegroup, a chrysene group, a cyclopentadiene group, atetrahydronaphthalene group, a furan group, a thiophene group, a silolegroup, an indene group, a fluorene group, an indole group, a carbazolegroup, a benzofuran group, a dibenzofuran group, a benzothiophene group,a dibenzothiophene group, a benzosilole group, a dibenzosilole group, anindenopyridine group, an indolopyridine group, a benzofuropyridinegroup, a benzothienopyridine group, a benzosilolopyridine group, anindenopyrimidine group, an indolopyrimidine group, a benzofuropyrimidinegroup, a benzothienopyrimidine group, a benzosilolopyrimidine group, adihydropyridine group, a pyridine group, a pyrimidine group, a pyrazinegroup, a pyridazine group, a triazine group, a quinoline group, anisoquinoline group, a quinoxaline group, a quinazoline group, aphenanthroline group, a benzoquinoline group, a benzoisoquinoline group,a benzoquinoxaline group, a benzoquinazoline group, a pyrrole group, apyrazole group, an imidazole group, a dihydroimidazole group, a triazolegroup, a dihydrotriazole group, an oxazole group, an iso-oxazole group,a thiazole group, an isothiazole group, an oxadiazole group, athiadiazole group, a benzopyrazole group, a benzimidazole group, adihydrobenzimidazole group, an imidazopyridine group, adihydroimidazopyridine group, an imidazopyrimidine group, adihydroimidazopyrimidine group, an imidazopyrazine group, adihydroimidazopyrazine group, a benzoxazole group, a benzothiazolegroup, a benzoxadiazole group, a benzothiadiazole group, atetrahydroisoquinoline group, and a tetrahydroquinoline group, butembodiments of the present disclosure are not limited thereto.

In some embodiments, in Formula 1-1, A₁₁ to A₁₆ may each independentlybe selected from a benzene group, a naphthalene group, an indene group,a fluorene group, an indole group, a carbazole group, a benzofurangroup, a dibenzofuran group, a benzothiophene group, a dibenzothiophenegroup, a pyridine group, a pyrimidine group, a pyrazine group, apyridazine group, a triazine group, a quinoline group, an isoquinolinegroup, a quinoxaline group, a quinazoline group, a pyrazole group, animidazole group, a dihydroimidazole group, a triazole group, adihydrotriazole group, an oxazole group, an iso-oxazole group, athiazole group, an isothiazole group, an oxadiazole group, a thiadiazolegroup, a benzopyrazole group, a benzimidazole group, adihydrobenzimidazole group, a dihydroimidazopyridine group, adihydroimidazopyrimidine group, a dihydroimidazopyrazine group, abenzoxazole group, and a benzothiazole group, but embodiments of thepresent disclosure are not limited thereto.

In some embodiments, in Formula 1-1, A₁₁ to A₁₆ may each independentlybe represented by one selected from Formulae 2-1 to 2-43, butembodiments of the present disclosure are not limited thereto:

In Formulae 2-1 to 2-43,

X₂₁ to X₂₃ may each independently be selected from C(R₂₄) and C—*,provided that at least two selected from X₂₁ to X₂₃ are each C—*,

X₂₄ may be N—*, and X₂₅ and X₂₆ may each independently be selected fromC(R₂₄) and C—*, provided that at least one selected from X₂₅ and X₂₆ isC—*,

X₂₇ and X₂₈ may each independently be selected from O, S, C(R₂₄), N,N(R₂₅), and N—*; and X₂₉ may be selected from O, S, C(R₂₄), and C—*,provided that i) at least one selected from X₂₇ and X₂₈ is N—*, and X₂₉is C—*, or ii) X₂₇ and X₂₈ are each N—*, and X₂₉ is selected from O, S,and C(R₂₄),

R₂₁ to R₂₄ may each independently be the same as R₁₁ in Formula 1,

b21 may be selected from 1, 2, and 3,

b22 may be selected from 1, 2, 3, 4, and 5,

b23 may be selected from 1, 2, 3, and 4,

b24 may be selected from 1 and 2, and

* indicates a binding site to an adjacent atom.

In some embodiments, in Formula 1-1, A₁ and A₁₂ may each independentlybe selected from an indole group, a carbazole group, a pyridine group, apyrimidine group, a pyrazine group, a pyridazine group, a triazinegroup, a quinoline group, an isoquinoline group, a quinoxaline group, aquinazoline group, a pyrazole group, an imidazole group, adihydroimidazole group, a triazole group, a dihydrotriazole group, anoxazole group, an iso-oxazole group, a thiazole group, an isothiazolegroup, an oxadiazole group, a thiadiazole group, a benzopyrazole group,a benzimidazole group, a dihydrobenzimidazole group, adihydroimidazopyridine group, a dihydroimidazopyrimidine group, adihydroimidazopyrazine group, a benzoxazole group, and a benzothiazolegroup, and

A₁₃ to A₁₆ may each independently be selected from a benzene group, anaphthalene group, an indene group, a fluorene group, a benzofurangroup, a dibenzofuran group, a benzothiophene group, and adibenzothiophene group, but embodiments of the present disclosure arenot limited thereto.

In some embodiments, in Formula 1-1, A₁₃ to A₁₆ may each independentlybe a benzene group, but embodiments of the present disclosure are notlimited thereto.

In Formula 1-1, X₁₁ to X₁₈ may each independently be selected from N andC.

In some embodiments, in Formula 1-1, X₁₁ to X₁₈ may each be C, butembodiments of the present disclosure are not limited thereto.

In Formula 1-1, Y₁₁ to Y₁₄ may each independently be selected from N, C,O, and S.

In some embodiments, in Formula 1-1, Y₁₁ to Y₁₄ may each independentlybe selected from N and C, but embodiments of the present disclosure arenot limited thereto.

In some embodiments, in Formula 1-1, Y₁₁ and Y₁₂ may each be C, butembodiments of the present disclosure are not limited thereto.

In Formula 1-1, i) Z₁₁ may be B, and Z₁₂ may be N, or ii) Z₁₁ may be N,and Z₁₂ may be B. In Formula 1-1, T₁₁ to T₁₄ may each independently beselected from a single bond, *—O—*′, *—S—*′, *—N(R₁₇)—*′, and*—C(R₁₇)(R₁₈)—*′. R₁₇ and R₁₈ are described below.

In some embodiments, in Formula 1-1, T₁₁ to T₁₄ may each be a singlebond, but embodiments of the present disclosure are not limited thereto.

In Formula 1-1, L₁₁ to L₁₃ may each independently be selected from asingle bond, *—O—*′, *—S—*′, *—C(R₁₉)(R₂₀)—*′, *—C(R₁₉)═*′, *═C(R₁₉)—*′,*—C(R₁₉)═C(R₂₀)—*, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R₁₉)—*′,*—N(R₁₉)—*′, *—P(R₁₉)—*′, *—Si(R₁₉)(R₂₀)—*, *—P(R₁₉)(R₂₀)—*′, and*—Ge(R₁₉)(R₂₀)—*′. R₁₉ and R₂₀ are described below.

In some embodiments, in Formula 1-1, L₁₁ to L₁₃ may each be a singlebond, but embodiments of the present disclosure are not limited thereto.

In Formula 1-1, a11 to a13 may respectively indicate the repeatingnumber of L₁₁(s) to L₁₃(S). a11 to a13 may each independently beselected from 0, 1, 2, and 3, provided that at least two selected froma11 to a13 are selected from 1, 2, and 3. When any of a11 to a13 are 2or greater, the at least two L₁₁(s) to L₁₃(S) may be identical to ordifferent from each other. When a11 is 0, A₁₁ and A₁₃ may not be linkedto each other. When a12 is 0, A₁₂ and A₁₄ may not be linked to eachother. When a13 is 0, A₁₁ and A₁₂ may not be linked to each other.

In some embodiments, in Formula 1-1, a11 and a12 may be selected from 1,2, and 3, but embodiments of the present disclosure are not limitedthereto.

In some embodiments, in Formula 1-1, a13 may be 0 or 1, but embodimentsof the present disclosure are not limited thereto.

In Formula 1-1, R₁₁ to R₂₀ may each independently be selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryloxy group, a substituted or unsubstitutedC₁-C₆₀ heteroarylthio group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —N(Q₁)(Q₂), —P(Q₁)(Q₂), —C(═O)(Q₁),—S(═O)(Q₁), —S(═O)₂(Q₁), —P(═O)(Q₁)(Q₂), and —P(═S)(Q₁)(Q₂). In someembodiments, at least two adjacent groups selected from R₁₁ to R₂₀ mayoptionally be bound to form a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀ heterocyclicgroup.

With respect to R₁₁ to R₂₀, Q₁ to Q₃ may each independently be selectedfrom hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amidino group, a hydrazino group, a hydrazonogroup, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a C₁-C₆₀ heteroaryloxygroup, a C₁-C₆₀ heteroarylthio group, a monovalent non-aromaticcondensed polycyclic group, a monovalent non-aromatic condensedheteropolycyclic group, a biphenyl group, and a terphenyl group.

In some embodiments, in Formula 1-1, R₁₁ to R₂₀ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, aphenyl group, a biphenyl group, and a terphenyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a perylenyl group, apentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an indolyl group, an isoindolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group,a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group,a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, abenzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group,a triazolyl group, a tetrazolyl group, a thiadiazolyl group, anoxadiazolyl group, a triazinyl group, a carbazolyl group, adibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group,a benzocarbazolyl group, a naphthobenzofuranyl group, anaphthobenzothiophenyl group, a naphthobenzosilolyl group, adibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenylgroup, a dinaphthosilolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinylgroup, a benzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, anindenopyrrolyl group, an indolopyrrolyl group, an indenocarbazolylgroup, and an indolocarbazolyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a perylenyl group, apentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an indolyl group, an isoindolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group,a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group,a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, abenzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group,a triazolyl group, a tetrazolyl group, a thiadiazolyl group, anoxadiazolyl group, a triazinyl group, a carbazolyl group, adibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group,a benzocarbazolyl group, a naphthobenzofuranyl group, anaphthobenzothiophenyl group, a naphthobenzosilolyl group, adibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenylgroup, a dinaphthosilolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinylgroup, a benzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, anindenopyrrolyl group, an indolopyrrolyl group, an indenocarbazolylgroup, and an indolocarbazolyl group, each substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a cyano group, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a biphenyl group, a terphenyl group, a pentalenyl group, anindenyl group, a naphthyl group, an azulenyl group, an indacenyl group,an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenylgroup, a pentacenyl group, a pyrrolyl group, a thiophenyl group, afuranyl group, a silolyl group, an imidazolyl group, a pyrazolyl group,a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an indolyl group, an isoindolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a benzoisoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, abenzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinylgroup, a cinnolinyl group, a phenanthridinyl group, an acridinyl group,a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, a benzosilolyl group, abenzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, abenzoisoxazolyl group, a triazolyl group, a tetrazolyl group, athiadiazolyl group, an oxadiazolyl group, a triazinyl group, acarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, adibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranylgroup, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, adibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenylgroup, a dinaphthosilolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinylgroup, a benzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, anindenopyrrolyl group, an indolopyrrolyl group, an indenocarbazolylgroup, an indolocarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁) (Q₃₂), —C(═O)(Q₃₁), —S(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂),and —P(═S)(Q₃₁)(Q₃₂); and

—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)(Q₁),—S(═O)₂(Q₁), —P(═O)(Q₁)(Q₂), and —P(═S)(Q₁)(Q₂),

wherein Q₁ to Q₃ and Q₃₁ to Q₃₃ may each independently be selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group, but embodiments of the present disclosureare not limited thereto.

In some embodiments, in Formula 1-1, R₁₁ to R₂₀ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group,and a C₁-C₂₀ alkyl group;

a C₁-C₂₀ alkyl group substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, and a cyano group;

groups represented by Formulae 5-1 to 5-138; and

—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)(Q₁),—S(═O)₂(Q₁), —P(═O)(Q₁)(Q₂), and —P(═S)(Q₁)(Q₂), but embodiments of thepresent disclosure are not limited thereto:

In Formulae 5-1 to 5-138,

X₅₁ may be selected from O, S, N(R₅₁), and C(R₅₁)R₆₀),

X₅₂ may be N or C(R₅₂), X₅₃ may be N or C(R₅₃), X₅₄ may be N or C(R₅₄),X₅₅ may be N or C(R₅₅), X₅₆ may be N or C(R₅₆), X₅₇ may be N or C(R₅₇),X₅₅ may be N or C(R₅₈), and X₅₉ may be N or C(R₅₉),

R₅₁ to R₆₀ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a thiophenyl group, a furanyl group, a silolyl group, acarbazolyl group, an indolyl group, an isoindolyl group, a benzofuranylgroup, a benzothiophenyl group, a benzosilolyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃),—N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)(Q₃₁), —S(═O)₂(Q₃₁),—P(═O)(Q₃₁)(Q₃₂), and —P(═S)(Q₃₁)(Q₃₂),

wherein Q₁ to Q₃ and Q₃₁ to Q₃₃ may each independently be selected froma C₁-C₆₀ alkyl group, a phenyl group, a biphenyl group, and a terphenylgroup,

b51 may be selected from 1, 2, 3, 4, and 5,

b52 may be selected from 1, 2, 3, 4, 5, 6, and 7,

b53 may be selected from 1, 2, 3, 4, 5, 6, 7, 8, and 9,

b54 may be selected from 1, 2, 3, and 4,

b55 may be selected from 1, 2, and 3,

b56 may be selected from 1 and 2,

b57 may be selected from 1, 2, 3, 4, 5, and 6, and

* indicates a binding site to an adjacent atom.

In some embodiments, in Formula 1-1, R₁₁ to R₂₀ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group,and a C₁-C₂₀ alkyl group;

a C₁-C₂₀ alkyl group substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, and a cyano group; and

a group represented by Formula 5-1, but embodiments of the presentdisclosure are not limited thereto.

In some embodiments, in Formula 1-1, R₁₁ and R₁₂ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group,and a C₁-C₂₀ alkyl group;

a C₁-C₂₀ alkyl group substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, and a cyano group; and

a group represented by Formula 5-1, and

R₁₃ to R₁₆ may each be hydrogen, but embodiments of the presentdisclosure are not limited thereto.

In some embodiments, in Formula 1-1, R₁₁ to R₂₀ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, amethyl group, an ethyl group, an n-propyl group, an iso-propyl group, ann-butyl group, iso-butyl group, a sec-butyl group, and a tert-butylgroup;

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,an n-butyl group, iso-butyl group, a sec-butyl group, and a tert-butylgroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, and a cyano group; and

groups represented by Formulae 6-1 to 6-257, but embodiments of thepresent disclosure are not limited thereto:

In Formulae 6-1 to 6-257,

“i-Pr” represents an iso-propyl group,

“t-Bu” represents a tert-butyl group,

“Ph” represents a phenyl group,

“1-Naph” represents a 1-naphthyl group,

“2-Naph” represents a 2-naphthyl group, and

* indicates a binding site to an adjacent atom.

In some embodiments, in Formula 1-1, R₁₁ to R₁₆ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, amethyl group, an ethyl group, an n-propyl group, an iso-propyl group, ann-butyl group, iso-butyl group, a sec-butyl group, and a tert-butylgroup;

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,an n-butyl group, iso-butyl group, a sec-butyl group, and a tert-butylgroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, and a cyano group; and

groups represented by Formulae 6-1 to 6-110, but embodiments of thepresent disclosure are not limited thereto:

In some embodiments, in Formula 1-1, R₁₁ and R₁₂ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, amethyl group, an ethyl group, an n-propyl group, an iso-propyl group, ann-butyl group, iso-butyl group, a sec-butyl group, and a tert-butylgroup;

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group,an n-butyl group, iso-butyl group, a sec-butyl group, and a tert-butylgroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, and a cyano group; and

groups represented by Formulae 6-1 to 6-31, but embodiments of thepresent disclosure are not limited thereto.

In some embodiments, in Formula 1-1, R₁₃ to R₁₆ may each be hydrogen,but embodiments of the present disclosure are not limited thereto.

In Formula 1-1, b11 to b16 may respectively indicate the number ofR₁₁(s) to R₁₆(S). b11 to b16 may each independently be selected from 1,2, 3, 4, 5, 6, 7, and 8. When any of b11 to b16 are 2 or greater, the atleast two R₁₁(s) to R₁₆(s) may be identical to or different from eachother.

In Formula 1-1, *1 to *4 may each independently be a binding site to M₁.

In Formula 1-1, * and *′ each indicate a binding site to an adjacentatom.

In some embodiments, in Formula 1, L₁ may be a ligand represented by oneselected from Formulae 1-11 and 1-12, but embodiments of the presentdisclosure are not limited thereto:

In Formulae 1-11 and 1-12,

*1 to *4, A₁₁ to A₁₆, Y₁₁ to Y₁₄, L₁₁, L₁₂, a11, a12, R₁₁ to R₁₆, andb11 to b16 may each independently be the same as defined in connectionwith Formula 1-1.

In some embodiments, in Formula 1, L₁ may be a ligand represented by oneselected from Formulae 1-21 and 1-22, but embodiments of the presentdisclosure are not limited thereto:

In Formulae 1-21 and 1-22,

*1 to *4, A₁₁, A₁₂, A₁₅, A₁₆, Y₁₁ to Y₁₄, L₁₁, L₁₂, a11, a12, R₁₁ toR₁₆, and b1 to b16 may each independently be the same defined inconnection with Formula 1-1.

In some embodiments, L₁ may be a ligand represented by one selected fromFormulae 1-31 and 1-32, but embodiments of the present disclosure arenot limited thereto:

In Formulae 1-31 and 1-32,

*1 to *4, A₁₁, A₁₂, Y₁₃, Y₁₄, L₁₁, L₁₂, a11, a12, R₁₁, R₁₂, and b11 tob16 may each independently be defined the same as defined in connectionwith Formula 1-1, and

R_(13a), R_(13b), R_(14a), R_(14b), R_(15a) to R_(15d), and R_(16a) toR_(16d) may each independently be the same as R₁₃ in Formula 1-1.

In Formula 1, L₂ may be selected from a monodentate ligand and abidentate ligand.

In some embodiments, in Formula 1, L₂ may be a ligand represented by oneselected from Formulae 7-1 to 7-11, but embodiments of the presentdisclosure are not limited thereto:

In Formulae 7-1 to 7-11,

A₇₁ and A₇₂ may each independently be selected from a C₅-C₂₀ carbocyclicgroup and a C₁-C₂₀ heterocyclic group,

X₇₁ and X₇₂ may each independently be selected from C and N,

X₇₃ may be N or C(Q₇₃), X₇₄ may be N or C(Q₇₄), X₇₅ may be N or C(Q₇₅),X₇₆ may be N or C(Q₇₆), and X₇₇ may be N or C(Q₇₇),

X₇₈ may be O, S, or N(Q₇₈), and X₇₉ may be O, S, or N(Q₇₉),

Y₇₁ and Y₇₂ may each independently be selected from a single bond, adouble bond, a substituted or unsubstituted C₁-C₅ alkylene group, asubstituted or unsubstituted C₂-C₅ alkenylene group, and a substitutedor unsubstituted C₆-C₁₀ arylene group,

Z₇₁ and Z₇₂ may each independently be selected from N, O, N(R₇₅),P(R₇₅)(R₇₆), and As(R₇₅)(R₇₆),

Z₇₃ may be selected from P and As,

Z₇₄ may be selected from CO (e.g., a carbonyl moiety, C(═O)) andC(R₇₅)(R₇₆),

R₇₁ to R₈₀ and Q₇₃ to Q₇₉ may each independently be selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a carboxylic acid group or a salt thereof, a sulfonicacid group or a salt thereof, a phosphoric acid group or a salt thereof,a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, and asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, wherein R₇₁ and R₇₂ may optionally be bound toform a ring, R₇₇ and R₇₈ may optionally be bound to form a ring, R₇₈ andR₇₉ may optionally be bound to form a ring, and R₇₉ and R₈₀ mayoptionally be bound to form a ring,

b71 and b72 may each independently be selected from 1, 2, and 3, and

* and *′ each indicate a binding site to an adjacent atom.

In some embodiments, in Formula 7-1, A₇₁ and A₇₂ may each independentlybe selected from a benzene group, a naphthalene group, an imidazolegroup, a benzimidazole group, a pyridine group, a pyrimidine group, atriazine group, a quinoline group, and an isoquinoline group, butembodiments of the present disclosure are not limited thereto.

In some embodiments, in Formula 7-1, X₇₂ and X₇₉ may each be N, butembodiments of the present disclosure are not limited thereto.

In some embodiments, in Formula 7-7, X₇₃ may be C(Q₇₃), X₇₄ may beC(Q₇₄), X₇₅ may be C(Q₇₅), X₇₆ may be C(Q₇₆), and X₇₇ may be C(Q₇₇), butembodiments of the present disclosure are not limited thereto.

In some embodiments, in Formula 7-8, X₇₈ may be N(Q₇₈), and X₇₉ may beN(Q₇₉), but embodiments of the present disclosure are not limitedthereto.

In some embodiments, in Formulae 7-2, 7-3, and 7-8, Y₇₁ and Y₇₂ may eachindependently be selected from a substituted or unsubstituted methylenegroup and a substituted or unsubstituted phenylene group, butembodiments of the present disclosure are not limited thereto.

In some embodiments, in Formulae 7-1 and 7-2, Z₇₁ and Z₇₂ may each be O,but embodiments of the present disclosure are not limited thereto.

In some embodiments, in Formula 7-4, Z₇₃ may be P, but embodiments ofthe present disclosure are not limited thereto.

In some embodiments, in Formulae 7-1 to 7-8, R₇₁ to R₈₀ and Q₇₃ to Q₇₉may each independently be selected from hydrogen, deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group,an amidino group, a hydrazine group, a hydrazone group, a carboxylicacid group or a salt thereof, a sulfonic acid group or a salt thereof, aphosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, and aC₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazine group, a hydrazone group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a phenyl group, a naphthyl group, a pyridinylgroup, and a pyrimidinyl group;

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, and animidazopyridinyl group; and

a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, an imidazolyl group, a pyrazolylgroup, a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an isoindolyl group, an indolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group,a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group,an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, atriazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, abenzocarbazolyl group, a dibenzocarbazolyl group, and animidazopyridinyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, -CD₃, -CD₂H, -CDH₂, —CF₃, —CF₂H, —CFH₂, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a phenyl group, a naphthyl group, a fluorenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolylgroup, a thiophenyl group, a furanyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, aquinazolinyl group, a cinnolinyl group, a carbazolyl group, aphenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group,an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolylgroup, and an imidazopyridinyl group, but embodiments of the presentdisclosure are not limited thereto.

In some embodiments, in Formula 1, L₂ may be a ligand represented by oneselected from Formulae 8-1 to 8-11, but embodiments of the presentdisclosure are not limited thereto:

In Formulae 8-1 to 8-11, * indicates a binding site to an adjacent atom.

In Formula 1, n1 indicates the number of L₁(s), and n1 may be 1.

In Formula 1, n2 indicates the number of L₂(s), and n2 may be selectedfrom 0, 1, and 2.

In some embodiments, in Formula 1, n1 may be 1, and n2 may be 0, butembodiments of the present disclosure are not limited thereto.

In some embodiments, in Formula 1, n1 may be 1, and n2 may be 1 or 2,but embodiments of the present disclosure are not limited thereto.

In some embodiments, in Formula 1, M₁ may be selected from Pt and Pd, n1may be 1, and n2 may be 0, but embodiments of the present disclosure arenot limited thereto.

In some embodiments, the organometallic compound represented by Formula1 may be selected from Compounds 1 to 240, but embodiments of thepresent disclosure are not limited thereto:

The organometallic compound represented by Formula 1 may emit blue lighthaving a maximum emission wavelength of about 450 nm or greater and lessthan 490 nm.

The organometallic compound represented by Formula 1 includes anazaborine moiety. When the organometallic compound represented byFormula 1 is included in an emission layer of an organic light-emittingdevice, formation of an excimer and an exciplex with a host may besuppressed. Accordingly, the colorimetric purity and lifespan of anorganic light-emitting device including the organometallic compound maybe improved.

In the organometallic compound represented by Formula 1, a metal atommay bind to an α-position of a boron (B) or nitrogen (N) atom. As such,metal-ligand charge transfer in the complex may be improved.Accordingly, the luminescent efficiency and lifespan of an organiclight-emitting device including the organometallic compound may beimproved.

In the organometallic compound represented by Formula 1, B and N may bedirectly linked to each other via a single bond, and the organometalliccompound may have a multi-ring structure in which the B and N atoms aresurrounded by rings. Accordingly, the organometallic compound may haveimproved structural durability. Accordingly, an organic light-emittingdevice including the organometallic compound may have improvedluminescent efficiency.

The organometallic compound represented by Formula 1 may be synthesizedusing any suitable organic synthetic method. Methods of synthesizing theorganometallic compound may be understood by those having ordinary skillin the art by referring to Examples described herein.

At least one organometallic compound represented by Formula 1 may beincluded between a pair of electrodes in an organic light-emittingdevice. In some embodiments, the organometallic compound may be includedin at least one selected from a hole transport region, an electrontransport region, and an emission layer.

In some embodiments, the organometallic compound represented by Formula1 may be used as a material for forming a capping layer positioned onone or both outer side of the pair of electrodes in an organiclight-emitting device.

In some embodiments, the emission layer may include the organometalliccompound, but embodiments of the present disclosure are not limitedthereto.

In some embodiments, the emission layer may include a host and theorganometallic compound, and an amount of the host in the emission layermay be greater than an amount of the organometallic compound in theemission layer, but embodiments of the present disclosure are notlimited thereto.

As used herein, expressions such as “at least one organometalliccompound represented by Formula 1” and “(layer) may include at least oneorganometallic compound” indicate that “(the organic layer) may includeone organometallic compound of Formula 1, or may include two or moredifferent organometallic compounds of Formula 1”.

For example, a single organometallic compound, referred to as Compound1, may be included in the organic layer. In this embodiment, Compound 1may be included in the emission layer of the organic light-emittingdevice. In some embodiments, two organometallic compounds, referred toas Compounds 1 and 2, may both be included in the organic layer. In thisembodiment, Compounds 1 and 2 may be present in the same layer (forexample, Compounds 1 and 2 may both be (e.g., simultaneously) present inthe emission layer), or may be present in different layers (for example,Compound 1 may be present in the emission layer, and Compound 2 may bepresent in an electron transport layer).

The organic layer may include: i) a hole transport region between thefirst electrode (anode) and the emission layer, which may include atleast one selected from a hole injection layer, a hole transport layer,a buffer layer, and an electron blocking layer, and ii) an electrontransport region between the emission layer and the second electrode(cathode), which may include at least one selected from a hole blockinglayer, an electron transport layer, and an electron injection layer. Theemission layer may include the at least one organometallic compoundrepresented by Formula 1.

The term “organic layer” as used herein may refer to a single layerand/or a plurality of layers between the first electrode and the secondelectrode in an organic light-emitting device. Materials included in the“organic layer” are not limited to being an organic material.

Description of FIG. 1

FIG. 1 is a schematic view of an organic light-emitting device 10according to an example embodiment of the present disclosure. Theorganic light-emitting device 10 may include a first electrode 110, anorganic layer 150, and a second electrode 190.

Hereinafter, the structure of the organic light-emitting device 10according to an embodiment of the present disclosure and a method ofmanufacturing an organic light-emitting device according to anembodiment of the present disclosure will be described in connectionwith FIG. 1.

First Electrode 110

In FIG. 1, a substrate may be positioned under the first electrode 110or above the second electrode 190. The substrate may be a glasssubstrate and/or a plastic substrate having excellent mechanicalstrength, thermal stability, transparency, surface smoothness, ease ofhandling, and/or water resistance.

The first electrode 110 may be formed by depositing and/or sputtering,onto the substrate, a material for forming the first electrode 110. Whenthe first electrode 110 is an anode, the material for forming the firstelectrode 110 may be selected from materials with a high work functionto facilitate hole injection.

The first electrode 110 may be a reflective electrode, asemi-transmissive electrode, or a transmissive electrode. When the firstelectrode 110 is a transmissive electrode, the material for forming thefirst electrode 110 may be selected from indium tin oxide (ITO), indiumzinc oxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), and combinationsthereof, but embodiments of the present disclosure are not limitedthereto. In some embodiments, when the first electrode 110 is asemi-transmissive electrode or a reflective electrode, at least oneselected from magnesium (Mg), silver (Ag), aluminum (Al),aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In),magnesium-silver (Mg—Ag), and combinations thereof may be used as amaterial for forming the first electrode 110, but embodiments of thepresent disclosure are not limited thereto.

The first electrode 110 may have a single-layered structure, or amulti-layered structure including two or more layers. In someembodiments, the first electrode 110 may have a triple-layered structureof ITO/Ag/ITO, but embodiments of the present disclosure are not limitedthereto.

Organic Layer 150

The organic layer 150 may be on the first electrode 110. The organiclayer 150 may include an emission layer.

In some embodiments, the organic layer 150 may further include a holetransport region between the first electrode 110 and the emission layer,and/or an electron transport region between the emission layer and thesecond electrode 190.

Hole Transport Region in Organic Layer 150

The hole transport region may have: i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The hole transport region may include at least one selected from a holeinjection layer, a hole transport layer, an emission auxiliary layer,and/or an electron blocking layer.

For example, the hole transport region may have a single-layeredstructure including a single layer including a plurality of differentmaterials, or a multi-layered structure, e.g., a hole injectionlayer/hole transport layer structure, a hole injection layer/holetransport layer/emission auxiliary layer structure, a hole injectionlayer/emission auxiliary layer structure, a hole transportlayer/emission auxiliary layer structure, or a hole injection layer/holetransport layer/electron blocking layer structure, wherein layers ofeach structure are sequentially stacked on the first electrode 110 ineach stated order, but embodiments of the present disclosure are notlimited thereto.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB (NPD), p-NPB, TPD, a spiro-TPD, aspiro-NPB, methylated-NPB, TAPC, HMTPD,4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (PANI/CSA),(polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), a compoundrepresented by Formula 201, and a compound represented by Formula 202:

In Formulae 201 and 202,

L₂₀₁ to L₂₀₄ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

L₂₀₅ may be selected from *—O—*′, *—S—*′, *—N(Q₂₀₁)-*′, a substituted orunsubstituted C₁-C₂₀ alkylene group, a substituted or unsubstitutedC₂-C₂₀ alkenylene group, a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xa1 to xa4 may each independently be an integer from 0 to 3,

xa5 may be an integer from 1 to 10, and

R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independently be selected from asubstituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted orunsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In some embodiments, in Formula 202, R₂₀₁ and R₂₀₂ may optionally bebound via a single bond, a dimethyl-methylene group, or adiphenyl-methylene group, and R₂₀₃ and R₂₀₄ may optionally be bound viaa single bond, a dimethyl-methylene group, or a diphenyl-methylenegroup.

In some embodiments, in Formula 201 and 202, L₂₀₁ to L₂₀₅ may eachindependently be selected from:

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂),

wherein Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group.

In some embodiments, xa1 to xa4 may each independently be 0, 1, or 2.

In some embodiments, xa5 may be 1, 2, 3, or 4.

In some embodiments, R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independently beselected from a phenyl group, a biphenyl group, a terphenyl group, apentalenyl group, an indenyl group, a naphthyl group, an azulenyl group,a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂),

wherein Q₃₁ to Q₃₃ may each be the same as described herein.

In some embodiments, in Formula 201, at least one selected from R₂₀₁ toR₂₀₃ may each independently be selected from:

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a phenyl group substituted with a C₁-C₁₀ alkylgroup, a phenyl group substituted with —F, a naphthyl group, a fluorenylgroup, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group, but embodiments of the presentdisclosure are not limited thereto.

In some embodiments, in Formula 202, i) R₂₀₁ and R₂₀₂ may be bound via asingle bond, and/or ii) R₂₀₃ and R₂₀₄ may be bound via a single bond.

In some embodiments, in Formula 202, at least one selected from R₂₀₁ toR₂₀₄ may be selected from:

a carbazolyl group; and

a carbazolyl group substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, acarbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,but embodiments of the present disclosure are not limited thereto.

In some embodiments, the compound represented by Formula 201 may befurther represented by Formula 201A:

In some embodiments, the compound represented by Formula 201 may befurther represented by Formula 201A(1), but embodiments of the presentdisclosure are not limited thereto:

In some embodiments, the compound represented by Formula 201 may befurther represented by Formula 201A-1, but embodiments of the presentdisclosure are not limited thereto:

In some embodiments, the compound represented by Formula 202 may befurther represented by Formula 202A:

In some embodiments, the compound represented by Formula 202 may befurther represented by Formula 202A-1:

In Formulae 201A, 201A(1), 201A-1, 202A, and 202A-1, L₂₀₁ to L₂₀₃, xa1to xa3, xa5, and R₂₀₂ to R₂₀₄ may be the same as described herein,

R₂₁₁ and R₂₁₂ may each be the same as R₂₀₃, and

R₂₁₃ to R₂₁₇ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group.

The hole transport region may include at least one compound selectedfrom Compounds HT1 to HT39, but embodiments of the present disclosureare not limited thereto:

The thickness of the hole transport region may be about 100 Angstroms(Å) to about 10,000 Å, for example, about 100 Å to about 1,000 Å. Whenthe hole transport region includes at least one selected from a holeinjection layer and a hole transport layer, the thickness of the holeinjection layer may be about 100 Å to about 9,000 Å, for example, about100 Å to about 1,000 Å, while the thickness of the hole transport layermay be about 50 Å to about 2,000 Å, for example, about 100 Å to about1,500 Å. When the thicknesses of the hole transport region, the holeinjection layer, and/or the hole transport layer are within any of theseranges, excellent hole transport characteristics may be obtained withouta substantial increase in driving voltage.

The emission auxiliary layer may increase light emission efficiency bycompensating for an optical resonance distance according to thewavelength of light emitted by an emission layer (e.g., adjusting theoptical resonance distance within the device to match the wavelength oflight emitted from the emission layer). The electron blocking layer mayreduce or eliminate the flow of electrons from an electron transportregion. The emission auxiliary layer and the electron blocking layer mayeach include the aforementioned materials.

p-Dopant

The hole transport region may include a charge generating material inaddition to the aforementioned materials in order to improve conductiveproperties of the hole transport region. The charge generating materialmay be substantially homogeneously or non-homogeneously dispersed in thehole transport region.

The charge-generating material may be, for example, a p-dopant.

In some embodiments, a lowest unoccupied molecular orbital (LUMO) energylevel of the p-dopant may be −3.5 eV or less.

The p-dopant may include at least one selected from a quinonederivative, a metal oxide, and a cyano group-containing compound, butembodiments of the present disclosure are not limited thereto.

In some embodiments, the p-dopant may be selected from a quinonederivative (such as tetracyanoquinodimethane (TCNQ) and/or2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ));

a metal oxide (such as tungsten oxide and/or molybdenum oxide);

1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and

a compound represented by Formula 221, but embodiments of the presentdisclosure are not limited thereto:

In Formula 221,

R₂₂₁ to R₂₂₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, wherein at least oneselected from R₂₂₁ to R₂₂₃ may include at least one substituent selectedfrom a cyano group, —F, —Cl, —Br, —I, a C₁-C₂₀ alkyl group substitutedwith —F, a C₁-C₂₀ alkyl group substituted with —Cl, a C₁-C₂₀ alkyl groupsubstituted with —Br, and a C₁-C₂₀ alkyl group substituted with —I.

Emission Layer in Organic Layer 150

When the organic light-emitting device 10 is a full color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, and/or a blue emission layer,according to a sub-pixel. In one or more embodiments, the emission layermay have a stacked structure. The stacked structure may include two ormore layers selected from a red emission layer, a green emission layer,and a blue emission layer. In some embodiments, the two or more layersmay be in direct contact with each other. In some embodiments, the twoor more layers may be separated from each other. In one or moreembodiments, the emission layer may include two or more materials. Thetwo or more materials may include a red light-emitting material, a greenlight-emitting material, and/or a blue light-emitting material. In someembodiments, the two or more materials may be mixed with each other in asingle layer. The two or more materials mixed with each other in thesingle layer may emit white light.

The emission layer may include a host and a dopant. The dopant mayinclude the organometallic compound represented by Formula 1. In someembodiments, the dopant may include at least one of a phosphorescentdopant and a fluorescent dopant, in addition to the organometalliccompound represented by Formula 1.

The amount of the dopant in the emission layer may be about 0.01 partsto about 15 parts by weight based on 100 parts by weight of the host,but embodiments of the present disclosure are not limited thereto.

The thickness of the emission layer may be about 100 Å to about 1,000 Å,and in some embodiments, about 200 Å to about 600 Å. When the thicknessof the emission layer is within these ranges, improved luminescencecharacteristics may be obtained without a substantial increase indriving voltage.

Host in Emission Layer

The host may include a compound represented by Formula 301:

[Ar₃₀₁]_(xb11)-[(L₃₀₁)_(xb1)-R₃₀₁]_(xb21).  Formula 301

In Formula 301,

Ar₃₀₁ may be selected from a substituted or unsubstituted C₅-C₆₀carbocyclic group and a substituted or unsubstituted C₁-C₆₀ heterocyclicgroup,

xb11 may be 1, 2, or 3,

L₃₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xb1 may be an integer from 0 to 5,

R₃₀₁ may be selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂),—B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), and —P(═O)(Q₃₀₁) (Q₃₀₂),and

xb21 may be an integer from 1 to 5,

wherein Q₃₀₁ to Q₃₀₃ may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group, but embodiments of the presentdisclosure are not limited thereto.

In some embodiments, in Formula 301, Ar₃₀₁ may be selected from:

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup; and

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

wherein Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group, but embodiments of the presentdisclosure are not limited thereto.

When xb11 in Formula 301 is 2 or greater, the at least two Ar₃₀₁(S) maybe bound (linked) via a single bond.

In one or more embodiments, the compound represented by Formula 301 maybe further represented by Formula 301-1 or Formula 301-2:

In Formulae 301-1 and 301-2,

A₃₀₁ to A₃₀₄ may each independently be selected from a benzene group, anaphthalene group, a phenanthrene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a pyridine group,a pyrimidine group, an indene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,an indole group, a carbazole group, a benzocarbazole group, adibenzocarbazole group, a furan group, a benzofuran group, adibenzofuran group, a naphthofuran group, a benzonaphthofuran group, adinaphthofuran group, a thiophene group, a benzothiophene group, adibenzothiophene group, a naphthothiophene group, a benzonapthothiophenegroup, and a dinaphthothiophene group,

X₃₀₁ may be O, S, or N-[(L₃₀₄)_(xb4)-R₃₀₄],

R₃₁₁ to R₃₁₄ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

xb22 and xb23 may each independently be 0, 1, or 2,

L₃₀₁, xb1, R₃₀₁, and Q₃₁ to Q₃₃ may each be the same as describedherein,

L₃₀₂ to L₃₀₄ may each independently be the same as L₃₀₁,

xb2 to xb4 may each independently be the same as xb1, and

R₃₀₂ to R₃₀₄ may each independently be the same as R₃₀₁.

In some embodiments, in Formulae 301, 301-1, and 301-2, L₃₀₁ to L₃₀₄ mayeach independently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, an azacarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

wherein Q₃₁ to Q₃₃ may each be the same as described herein.

In some embodiments, in Formulae 301, 301-1, and 301-2, R₃₀₁ to R₃₀₄ mayeach independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

wherein Q₃₁ to Q₃₃ may each be the same as described herein.

In some embodiments, the host may include an alkaline earth metalcomplex. For example, the host may include a beryllium (Be) complex,e.g., Compound H55 or a magnesium (Mg) complex. In some embodiments, thehost may include a zinc (Zn) complex.

The host may include at least one selected from9,10-di(2-naphthyl)anthracene (ADN),2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN),4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene(mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP),bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane),POPCPA(4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphineoxide (BCPDS), and Compounds H1 to H55, but embodiments of the presentdisclosure are not limited thereto:

In some embodiments, the host may include at least one selected from asilicon-containing compound (e.g., BCPDS and/or the like, as used in theExamples) and a phosphine oxide-containing compound (e.g., POPCPA and/orthe like, as used in the Examples).

The host may include one type or class of compounds, or in someembodiments, may include two or more different types or classes ofcompounds (for example, the Examples include BCPDS and POPCPA as hosts).As such, embodiments of the present disclosure may be modified invarious ways.

Phosphorescent Dopant Included in Emission Layer of Organic Layer 150

The phosphorescent dopant may include the organometallic compoundrepresented by Formula 1.

In some embodiments, the phosphorescent dopant may further include, inaddition to the organometallic compound represented by Formula 1, anorganometallic complex represented by Formula 401:

In Formulae 401 and 402,

M may be selected from iridium (Ir), platinum (Pt), palladium (Pd),osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu),terbium (Tb), rhodium (Rh), and thulium (Tm),

L₄₀₁ may be selected from ligands represented by Formula 402, and xc1may be 1, 2, or 3; where when xc1 is 2 or greater, at least two L₄₀₁(s)may be identical to or different from each other,

L₄₀₂ may be an organic ligand, and xc2 may be an integer selected from 0to 4; where when xc2 is 2 or greater, at least two L₄₀₂(S) may beidentical to or different from each other,

X₄₀₁ to X₄₀₄ may each independently be a nitrogen atom (N) or a carbonatom (C),

X₄₀₁ and X₄₀₃ may be bound to each other via a single bond or a doublebond, and X₄₀₂ and X₄₀₄ may be bound to each other via a single bond ora double bond,

A₄₀₁ and A₄₀₂ may each independently be a C₅-C₆₀ carbocyclic group or aC₁-C₆₀ heterocyclic group,

X₄₀₅ may be selected from a single bond, *—O—*′, *—S—*′, *—C(═O)—*′,*—N(Q₄₁₁)-*′, *—C(Q₄₁₁)(Q₄₁₂)-*′, *—C(Q₄₁₁)═C(Q₄₁₂)-*′, *—O(Q₄₁₁)=*′,and *═C(Q₄₁₁)=*′, wherein Q₄₁₁ and Q₄₁₂ may be selected from hydrogen,deuterium, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group,a biphenyl group, a terphenyl group, and a naphthyl group,

X₄₀₆ may be a single bond, O, or S,

R₄₀₁ and R₄₀₂ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, asubstituted or unsubstituted C₁-C₂₀ alkyl group, a substituted orunsubstituted C₁-C₂₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂),—B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁), —S(═O)₂(Q₄₀₁), and —P(═O)(Q₄₀₁)(Q₄₀₂),wherein Q₄₀₁ to Q₄₀₃ may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a C₆-C₂₀ aryl group, and a C₁-C₂₀heteroaryl group,

xc11 and xc12 may each independently be an integer from 0 to 10, and

* and *′ in Formula 402 each indicate a binding site to M in Formula401.

In some embodiments, in Formula 402, A₄₀₁ and A₄₀₂ may eachindependently be selected from a benzene group, a naphthalene group, afluorene group, a spiro-bifluorene group, an indene group, a pyrrolegroup, a thiophene group, a furan group, an imidazole group, a pyrazolegroup, a thiazole group, an isothiazole group, an oxazole group, anisoxazole group, a pyridine group, a pyrazine group, a pyrimidine group,a pyridazine group, a quinoline group, an isoquinoline group, abenzoquinoline group, a quinoxaline group, a quinazoline group, acarbazole group, a benzimidazole group, a benzofuran group, abenzothiophene group, an isobenzothiophene group, a benzoxazole group,an isobenzoxazole group, a triazole group, a tetrazole group, anoxadiazole group, a triazine group, a dibenzofuran group, and adibenzothiophene group.

In one or more embodiments, in Formula 402, i) X₄₀₁ may be nitrogen, andX₄₀₂ may be carbon, or ii) X₄₀₁ and X₄₀₂ may both (e.g., simultaneously)be nitrogen.

In some embodiments, in Formula 402, R₄₀₁ and R₄₀₂ may eachindependently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a phenyl group, a naphthyl group, a cyclopentyl group,a cyclohexyl group, an adamantyl group, a norbornanyl group, and anorbornenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantyl group, anorbornanyl group, a norbornenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantyl group, anorbornanyl group, a norbornenyl group a phenyl group, a biphenyl group,a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, atriazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornanylgroup, a norbornenyl group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and adibenzothiophenyl group; and

—Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁),—S(═O)₂(Q₄₀₁), and —P(═O)(Q₄₀₁) (Q₄₀₂),

wherein Q₄₀₁ to Q₄₀₃ may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group,and a naphthyl group, but embodiments of the present disclosure are notlimited thereto.

In one or more embodiments, when xc1 in Formula 401 is 2 or greater, twoA₄₀₁(S) of the at least two L₄₀₁(s) may optionally be bound via X₄₀₇ asa linking group, or two A₄₀₂(S) may optionally be bound via X₄₀₈ as alinking group (see, e.g., Compounds PD1 to PD4 and PD7). X₄₀₇ and X₄₀₈may each independently be selected from a single bond, *—O—*′, *—S—*′,*—C(═O)—*′, *—N(Q₄₁₃)-*′, *—C(Q₄₁₃)(Q₄₁₄)-*′, and *—C(Q₄₁₃)═C(Q₄₁₄)-*′,wherein Q₄₁₃ and Q₄₁₄ may each independently be hydrogen, deuterium, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenylgroup, a terphenyl group, or a naphthyl group, but embodiments of thepresent disclosure are not limited thereto.

L₄₀₂ in Formula 401 may be any suitable monovalent, divalent, ortrivalent organic ligand. For example, L₄₀₂ may be selected from ahalogen, a diketone (e.g., acetylacetonate), a carboxylic acid (e.g.,picolinate), —C(═O), an isonitrile group, —CN, and aphosphorus-containing group (e.g., phosphine or phosphite), butembodiments of the present disclosure are not limited thereto.

In some embodiments, the phosphorescent dopant may include, for example,at least one selected from Compounds PD1 to PD25, but embodiments of thepresent disclosure are not limited thereto:

Fluorescent Dopant in Emission Layer

The fluorescent dopant may include an arylamine compound or astyrylamine compound.

In some embodiments, the fluorescent dopant may include a compoundrepresented by Formula 501:

In Formula 501,

Ar₅₀₁ may be selected from a substituted or unsubstituted C₅-C₆₀carbocyclic group and a substituted or unsubstituted C₁-C₆₀ heterocyclicgroup,

L₅₀₁ to L₅₀₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xd1 to xd3 may each independently be an integer from 0 to 3,

R₅₀₁ and R₅₀₂ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,and

xd4 may be an integer from 1 to 6.

In some embodiments, in Formula 501, Ar₅₀₁ may be selected from:

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup; and

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, in Formula 501, L₅₀₁ to L₅₀₃ may eachindependently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, and a pyridinylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, and a pyridinylene group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group.

In some embodiments, in Formula 501, R₅₀₁ and R₅₀₂ may eachindependently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃),

wherein Q₃₁ to Q₃₃ may be selected from a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and anaphthyl group.

In one or more embodiments, xd4 in Formula 501 may be 2, but embodimentsof the present disclosure are not limited thereto.

In some embodiments, the fluorescent dopant may be selected fromCompounds FD1 to FD22:

In some embodiments, the fluorescent dopant may be selected from thefollowing compounds, but embodiments of the present disclosure are notlimited thereto:

Electron Transport Region in Organic Layer 150

The electron transport region may have: i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure each having aplurality of layers, each having a plurality of different materials.

The electron transport region may include at least one selected from abuffer layer, a hole blocking layer, an electron control layer, anelectron transport layer, and an electron injection layer, butembodiments of the present disclosure are not limited thereto.

In some embodiments, the electron transport region may have an electrontransport layer/electron injection layer structure, a hole blockinglayer/electron transport layer/electron injection layer structure, anelectron control layer/electron transport layer/electron injection layerstructure, or a buffer layer/electron transport layer/electron injectionlayer structure, wherein layers of each structure are sequentiallystacked on the emission layer in each stated order, but embodiments ofthe present disclosure are not limited thereto.

The electron transport region (for example, the buffer layer, the holeblocking layer, the electron control layer, and/or the electrontransport layer in the electron transport region) may include ametal-free compound including at least one π electron-depletednitrogen-containing ring.

The term “π electron-depleted nitrogen-containing ring” as used hereinrefers to a C₁-C₆₀ heterocyclic group having at least one *—N═*′ moietyas a ring-forming moiety.

For example, the “π electron-depleted nitrogen-containing ring” may be:i) a 5-membered to 7-membered heteromonocyclic group having at least one*—N═*′ moiety, ii) a heteropolycyclic group in which at least two5-membered to 7-membered heteromonocyclic groups, each having at leastone *—N═*′ moiety, are condensed, or iii) a heteropolycyclic group inwhich at least one of a 5-membered to 7-membered heteromonocyclic group,each having at least one *—N═*′ moiety, is condensed with at least oneC₅-C₆₀ carbocyclic group.

Non-limiting examples of the π electron-depleted nitrogen-containingring include an imidazole, a pyrazole, a thiazole, an isothiazole, anoxazole, an isoxazole, a pyridine, a pyrazine, a pyrimidine, apyridazine, an indazole, a purine, a quinoline, an isoquinoline, abenzoquinoline, a phthalazine, a naphthyridine, a quinoxaline, aquinazoline, a cinnoline, a phenanthridine, an acridine, aphenanthroline, a phenazine, a benzimidazole, an iso-benzothiazole, abenzoxazole, an isobenzoxazole, a triazole, a tetrazole, an oxadiazole,a triazine, a thiadiazole, an imidazopyridine, an imidazopyrimidine, andan azacarbazole, but embodiments of the present disclosure are notlimited thereto.

In some embodiments, the electron transport region may include acompound represented by Formula 601:

[Ar₆₀₁]_(xe11)-[(L₆₀₁)_(xe1)-R₆₀₁]_(xe21).  Formula 601

In Formula 601,

Ar₆₀₁ may be selected from a substituted or unsubstituted C₅-C₆₀carbocyclic group and a substituted or unsubstituted C₁-C₆₀ heterocyclicgroup,

xe11 may be 1, 2, or 3,

L₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xe1 may be an integer from 0 to 5,

R₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁),—S(═O)₂(Q₆₀₁), and —P(═O)(Q₆₀₁) (Q₆₀₂),

wherein Q₆₀₁ to Q₆₀₃ may each independently be a C₁-C₁₀ alkyl group, aC₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, or a naphthyl group, and

xe21 may be an integer from 1 to 5.

In some embodiments, at least one of the xe11 Ar₆₀₁(s) and the xe21R₆₀₁(s) in Formula 601 may include the π electron-depletednitrogen-containing ring.

In some embodiments, in Formula 601, Ar₆₀₁ may be selected from:

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an iso-benzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group; and

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an iso-benzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group,—Si(Q₃₁)(Q₃₂)(Q₃₃), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁) (Q₃₂),

wherein Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group.

When xe11 in Formula 601 is 2 or greater, the at least two Ar₆₀₁(S) maybe bound via a single bond.

In one or more embodiments, Ar₆₀₁ in Formula 601 may be an anthracenegroup.

In one or more embodiments, the compound represented by Formula 601 maybe further represented by Formula 601-1:

In Formula 601-1,

X₆₁₄ may be N or C(R₆₁₄), X₆₁₅ may be N or C(R₆₁₅), X₆₁₆ may be N orC(R₆₁₆), and at least one selected from X₆₁₄ to X₆₁₆ may be N,

L₆₁₁ to L₆₁₃ may each independently be the same as L₆₀₁,

xe611 to xe613 may each independently be the same as xe1,

R₆₁₁ to R₆₁₃ may each independently be the same as R₆₀₁, and

R₆₁₄ to R₆₁₆ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group.

In some embodiments, in Formulae 601 and 601-1, L₆₀₁ and L₆₁₁ to L₆₁₃may each independently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, and an azacarbazolyl group, but embodiments of the presentdisclosure are not limited thereto.

In one or more embodiments, xe1 and xe611 to xe613 in Formulae 601 and601-1 may each independently be 0, 1, or 2.

In some embodiments, in Formulae 601 and 601-1, R₆₀₁ and R₆₁₁ to R₆₁₃may each independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group;

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

—S(═O)₂(Q₆₀₁) and —P(═O)(Q₆₀₁)(Q₆₀₂),

wherein Q₆₀₁ and Q₆₀₂ may each independently be the same as describedherein.

The electron transport region may include at least one compound selectedfrom Compounds ET1 to ET36, but embodiments of the present disclosureare not limited thereto:

In some embodiments, the electron transport region may include at leastone compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline(BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq₃, BAlq,3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole(TAZ), NTAZ, and diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide(TSPO1):

The thicknesses of the buffer layer, the hole blocking layer, and/or theelectron control layer may each independently be about 20 Å to about1,000 Å, and in some embodiments, about 30 Å to about 300 Å. When thethicknesses of the buffer layer, the hole blocking layer and/or theelectron control layer are within these ranges, excellent hole blockingcharacteristics and/or excellent electron controlling characteristicsmay be obtained without a substantial increase in driving voltage.

The thickness of the electron transport layer may be about 100 Å toabout 1,000 Å, and in some embodiments, about 150 Å to about 500 Å. Whenthe thickness of the electron transport layer is within these ranges,excellent electron transport characteristics may be obtained without asubstantial increase in driving voltage.

The electron transport region (for example, the electron transport layerin the electron transport region) may further include, in addition tothe materials described above, a material including a metal.

The material including the metal may include at least one selected froman alkali metal complex and an alkaline earth metal complex. The alkalimetal complex may include a metal ion selected from a lithium (Li) ion,a sodium (Na) ion, a potassium (K) ion, a rubidium (Rb) ion, and acesium (Cs) ion. The alkaline earth metal complex may include a metalion selected from a beryllium (Be) ion, a magnesium (Mg) ion, a calcium(Ca) ion, a strontium (Sr) ion, and a barium (Ba) ion. Each ligandcoordinated with the metal ion in the alkali metal complex and/or withthe metal ion of the alkaline earth metal complex may independently beselected from a hydroxyquinoline, a hydroxyisoquinoline, ahydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, ahydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxydiphenyloxadiazole, a hydroxydiphenyl thiadiazole, a hydroxyphenyl pyridine, ahydroxyphenyl benzimidazole, a hydroxyphenyl benzothiazole, abipyridine, a phenanthroline, and a cyclopentadiene, but embodiments ofthe present disclosure are not limited thereto.

For example, the material including metal may include a Li complex. TheLi complex may include, e.g., Compound ET-D1 (lithium8-hydroxyquinolate, LiQ) and/or Compound ET-D2:

The electron transport region may include an electron injection layerthat facilitates injection of electrons from the second electrode 190.The electron injection layer may be in direct contact with the secondelectrode 190.

The electron injection layer may have: i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers, each including a plurality of different materials.

The electron injection layer may include an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal compound, an alkalineearth metal compound, a rare earth metal compound, an alkali metalcomplex, an alkaline earth metal complex, a rare earth metal complex, ora combination thereof.

The alkali metal may be selected from Li, Na, K, Rb, and Cs. In someembodiments, the alkali metal may be Li, Na, or Cs. In one or moreembodiments, the alkaline metal may be Li or Cs, but embodiments of thepresent disclosure are not limited thereto.

The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

The alkali metal compound, the alkaline earth metal compound, and therare earth metal compound may each independently be selected from oxidesand halides (e.g., fluorides, chlorides, bromides, and/or iodines) ofthe alkali metal, the alkaline earth metal, and the rare earth metal,respectively.

The alkali metal compound may be selected from alkali metal oxides (suchas Li₂O, Cs₂O, and/or K₂O) and alkali metal halides (such as LiF, NaF,CsF, KF, LiI, NaI, CsI, KI, and/or RbI). In some embodiments, the alkalimetal compound may be selected from LiF, Li₂O, NaF, LiI, NaI, CsI, andKI, but embodiments of the present disclosure are not limited thereto.

The alkaline earth-metal compound may be selected from alkalineearth-metal compounds (such as BaO, SrO, CaO, Ba_(x)Sr_(1-x)O (wherein0<x<1), and/or Ba_(x)Ca_(1-x)O (wherein 0<x<1)). In some embodiments,the alkaline earth metal compound may be selected from BaO, SrO, andCaO, but embodiments of the present disclosure are not limited thereto.

The rare earth metal compound may be selected from YbF₃, ScF₃, ScO₃,Y₂O₃, Ce₂O₃, GdF₃, and TbF₃. In some embodiments, the rare earth metalcompound may be selected from YbF₃, ScF₃, TbF₃, YbI₃, ScI₃, and TbI₃,but embodiments of the present disclosure are not limited thereto.

The alkali metal complex, the alkaline earth metal complex, and the rareearth metal complex may include ions of the above-described alkalimetal, alkaline earth metal, and rare earth metal, respectively. Eachligand coordinated with the metal ion of the alkali metal complex, thealkaline earth metal complex, and/or the rare earth metal complex mayindependently be selected from a hydroxyquinoline, ahydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, ahydroxyphenanthridine, a hydroxyphenyl oxazole, a hydroxyphenylthiazole, a hydroxydiphenyl oxadiazole, a hydroxydiphenyl thiadiazole, ahydroxyphenyl pyridine, a hydroxyphenyl benzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, and a cyclopentadiene,but embodiments of the present disclosure are not limited thereto.

The electron injection layer may include (e.g., consist of) an alkalimetal, an alkaline earth metal, a rare earth metal, an alkali metalcompound, an alkaline earth metal compound, a rare earth metal compound,an alkali metal complex, an alkaline earth metal complex, a rare earthmetal complex, or a combination thereof, as described above. In someembodiments, the electron injection layer may further include an organicmaterial. When the electron injection layer further includes an organicmaterial, the alkali metal, the alkaline earth metal, the rare earthmetal, the alkali metal compound, the alkaline earth metal compound, therare earth metal compound, the alkali metal complex, the alkaline earthmetal complex, the rare earth metal complex, or combination thereof maybe homogeneously or non-homogeneously dispersed in a matrix includingthe organic material.

The thickness of the electron injection layer may be about 1 Å to about100 Å, and in some embodiments, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within these ranges,excellent electron injection characteristics may be obtained without asubstantial increase in driving voltage.

Second Electrode 190

The second electrode 190 may be on the organic layer 150. In someembodiments, the second electrode 190 may be a cathode that is anelectron injection electrode. In this embodiment, a material for formingthe second electrode 190 may be a material having a low work function(such as a metal, an alloy, an electrically conductive compound, and/ora combination thereof).

The second electrode 190 may include at least one selected from lithium(Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium(Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver(Mg—Ag), ITO, and IZO, but embodiments of the present disclosure are notlimited thereto. The second electrode 190 may be a transmissiveelectrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 190 may have a single-layered structure, or amulti-layered structure including two or more layers.

Description of FIGS. 2 to 4

Referring to FIG. 2, an organic light-emitting device 20 includes afirst capping layer 210, the first electrode 110, the organic layer 150,and the second electrode 190, wherein the layers are sequentiallystacked in this stated order. Referring to FIG. 3, an organiclight-emitting device 30 includes the first electrode 110, the organiclayer 150, the second electrode 190, and a second capping layer 220,wherein the layers are sequentially stacked in this stated order.Referring to FIG. 4, an organic light-emitting device 40 includes thefirst capping layer 210, the first electrode 110, the organic layer 150,the second electrode 190, and the second capping layer 220, wherein thelayers are stacked in this stated order.

The first electrode 110, the organic layer 150, and the second electrode190 illustrated in FIGS. 2 to 4 may be substantially the same as thoseillustrated in FIG. 1.

In the organic light-emitting devices 20 and 40, light emitted from theemission layer in the organic layer 150 may pass through the firstelectrode 110 (which may be a semi-transmissive electrode or atransmissive electrode) and the first capping layer 210 to the outside.In the organic light-emitting devices 30 and 40, light emitted from theemission layer in the organic layer 150 may pass through the secondelectrode 190 (which may be a semi-transmissive electrode or atransmissive electrode) and the second capping layer 220 to the outside.

The first capping layer 210 and the second capping layer 220 may improvethe external luminescent efficiency based on the principle ofconstructive interference.

The first capping layer 210 and the second capping layer 220 may eachindependently be a capping layer including an organic material, aninorganic capping layer including an inorganic material, or a compositecapping layer including an organic material and an inorganic material.

At least one of the first capping layer 210 and the second capping layer220 may each independently include at least one material selected fromcarbocyclic compounds, heterocyclic compounds, amine-based compounds,porphyrin derivatives, phthalocyanine derivatives, naphthalocyaninederivatives, alkali metal complexes, and alkaline earth metal complexes.The carbocyclic compound, the heterocyclic compound, and the amine-basedcompound may optionally be substituted with a substituent containing atleast one element selected from O, N, S, Se, Si, F, Cl, Br, and I. Insome embodiments, at least one of the first capping layer 210 and thesecond capping layer 220 may each independently include an amine-basedcompound.

In one or more embodiments, at least one of the first capping layer 210and the second capping layer 220 may each independently include acompound represented by Formula 201 or a compound represented by 202.

In one or more embodiments, at least one of the first capping layer 210and the second capping layer 220 may each independently include acompound selected from Compounds HT28 to HT33 and Compound CP1 to CP5,but embodiments of the present disclosure are not limited thereto:

Hereinbefore, the organic light-emitting device has been described withreference to FIGS. 1 to 4, but embodiments of the present disclosure arenot limited thereto.

The layers constituting the hole transport region, the emission layer,and the layers constituting the electron transport region may each beformed in a set or predetermined region using one or more suitablemethods available in the art (such as vacuum deposition, spin coating,casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laserprinting, and laser-induced thermal imaging).

When layers constituting the hole transport region, the emission layer,and the layers constituting the electron transport region are eachindependently formed by vacuum deposition, the vacuum deposition may beperformed at a deposition temperature of about 100° C. to about 500° C.,at a vacuum degree of about 10⁻⁸ torr to about 10⁻³ torr, and at adeposition rate of about 0.01 Angstroms per second (A/sec) to about 100Å/sec, depending on the material to be included in each layer and thestructure of each layer to be formed.

When layers constituting the hole transport region, the emission layer,and the layers constituting the electron transport region are eachindependently formed by spin coating, the spin coating may be performedat a coating rate of about 2,000 revolutions per minute (rpm) to about5,000 rpm and at a heat treatment temperature of about 80° C. to 200°C., depending on the material to be included in each layer and thestructure of each layer to be formed.

General Definitions of Substituents

The term “first-row transition metal” as used herein refers to any ofthe metallic elements belonging to Period 4 and the first row of thed-block of the Periodic Table of Elements. Examples thereof includescandium (Sc), titanium (Ti), vanadium (V), chromium (Cr), manganese(Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), and zinc (Zn).

The term “second-row transition metal” as used herein refers to any ofthe metallic elements belonging to Period 5 and the second row of thed-block of the Periodic Table of Elements. Examples thereof includeyttrium (Y), zirconium (Zr), niobium (Nb), molybdenum (Mo), technetium(Tc), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), andcadmium (Cd).

The term “third-row transition metal” as used herein refers to any ofthe metallic elements belonging to Period 6 and the third row of thed-block/first row of f-block of the Periodic Table of Elements. Examplesthereof include lanthanum (La), samarium (Sm), europium (Eu), terbium(Tb), thulium (Tm), ytterbium (Yb), lutetium (Lu), hafnium (Hf),tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir),platinum (Pr), gold (Au), and mercury (Hg).

The term “C₁-C₆₀ alkyl group” as used herein refers to a linear orbranched aliphatic hydrocarbon monovalent group including 1 to 60 carbonatoms. Non-limiting examples thereof include a methyl group, an ethylgroup, a propyl group, an iso-butyl group, a sec-butyl group, atert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group.The term “C₁-C₆₀ alkylene group” as used herein refers to a divalentgroup having substantially the same structure as the C₁-C₆₀ alkyl group.

The term “C₂-C₆₀ alkenyl group” as used herein refers to a hydrocarbongroup including at least one carbon-carbon double bond in the middle orat the terminus of the C₂-C₆₀ alkyl group. Non-limiting examples thereofinclude an ethenyl group, a propenyl group, and a butenyl group. Theterm “C₂-C₆₀ alkenylene group” as used herein refers to a divalent grouphaving substantially the same structure as the C₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group” as used herein refers to a hydrocarbongroup including at least one carbon-carbon triple bond in the middle orat the terminus of the C₂-C₆₀ alkyl group. Non-limiting examples thereofinclude an ethynyl group and a propynyl group. The term “C₂-C₆₀alkynylene group” as used herein refers to a divalent group havingsubstantially the same structure as the C₂-C₆₀ alkynyl group.

The term “C₁-C₆₀ alkoxy group” as used herein refers to a monovalentgroup represented by —OA₁₀₁ (wherein A₁₀₁ is a C₁—C alkyl group).Non-limiting examples thereof include a methoxy group, an ethoxy group,and an isopropyloxy group.

The term “C₃-C₁₀ cycloalkyl group” as used herein refers to a monovalentsaturated hydrocarbon monocyclic group including 3 to 10 carbon atoms.Non-limiting examples thereof include a cyclopropyl group, a cyclobutylgroup, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.The term “C₃-C₁₀ cycloalkylene group” as used herein refers to adivalent group having substantially the same structure as the C₃-C₁₀cycloalkyl group.

The term “C₁-C₁₀ heterocycloalkyl group” as used herein refers to amonovalent monocyclic group including at least one heteroatom selectedfrom N, O, Si, P, and S as a ring-forming atom, and 1 to 10 carbonatoms. Non-limiting examples thereof include a 1,2,3,4-oxatriazolidinylgroup, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. Theterm “C₁-C₁₀ heterocycloalkylene group” as used herein refers to adivalent group having substantially the same structure as the C₁-C₁₀heterocycloalkyl group.

The term “C₃-C₁₀ cycloalkenyl group” as used herein refers to amonovalent monocyclic group including 3 to 10 carbon atoms and at leastone double bond in its ring, and which is not aromatic. Non-limitingexamples thereof include a cyclopentenyl group, a cyclohexenyl group,and a cycloheptenyl group. The term “C₃-C₁₀ cycloalkenylene group” asused herein refers to a divalent group having substantially the samestructure as the C₃-C₁₀ cycloalkenyl group.

The term “C₁-C₁₀ heterocycloalkenyl group” as used herein refers to amonovalent monocyclic group including at least one heteroatom selectedfrom N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms,and at least one double bond in its ring. Non-limiting examples of theC₁-C₁₀ heterocycloalkenyl group include a4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, anda 2,3-dihydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkylenegroup” as used herein refers to a divalent group having substantiallythe same structure as the C₁-C₁₀ heterocycloalkyl group.

The term “C₆-C₆₀ aryl group” as used herein refers to a monovalent grouphaving a carbocyclic aromatic system including 6 to 6 carbon atoms. Theterm “C₆-C₆₀ arylene group” as used herein refers to a divalent grouphaving a carbocyclic aromatic system including 6 to 60 carbon atoms.Non-limiting examples of the C₆-C₆₀ aryl group include a phenyl group, anaphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenylgroup, and a chrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀arylene group each independently include two or more rings, therespective rings may be fused (e.g., combined).

The term “C₁-C₆₀ heteroaryl group” as used herein refers to a monovalentgroup having a heterocyclic aromatic system including at least oneheteroatom selected from N, O, Si, P, and S as a ring-forming atom, and1 to 1 carbon atoms. The term “C₁-C₆₀ heteroarylene group” as usedherein refers to a divalent group having a heterocyclic aromatic systemincluding at least one heteroatom selected from N, O, Si, P, and S as aring-forming atom and 1 to 60 carbon atoms. Non-limiting examples of theC₁-C₆₀ heteroaryl group include a pyridinyl group, a pyrimidinyl group,a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, and an isoquinolinyl group. When the C₁-C₆₀ heteroaryl group andthe C₁-C₆₀ heteroarylene group each independently include two or morerings, the respective rings may be fused.

The term “C₆-C₆₀ aryloxy group” as used herein is represented by —OA₁₀₂(wherein A₁₀₂ is a C₆-C₆₀ aryl group). The term “C₆-C₆₀ arylthio group”as used herein is represented by —SA₁₀₃ (wherein A₁₀₃ is a C₆-C₆₀ arylgroup).

The term “C₁-C₆₀ heteroaryloxy group” as used herein refers to amonovalent group represented by —OA₁₀₄ (wherein A₁₀₄ is a C₁-C₆₀heteroaryl group). The term “C₁-C₆₀ heteroarylthio group” as used hereinrefers to a monovalent group represented by —SA₁₀₅ (wherein A₁₀₅ is aC₁-C₆₀ heteroaryl group).

The term “monovalent non-aromatic condensed polycyclic group” as usedherein refers to a monovalent group that has two or more condensed ringsand includes only carbon atoms as ring forming atoms (e.g., 8 to 60carbon atoms), wherein the entire molecular structure is non-aromatic. Anon-limiting example of the monovalent non-aromatic condensed polycyclicgroup includes a fluorenyl group. The term “divalent non-aromaticcondensed polycyclic group” as used herein refers to a divalent grouphaving substantially the same structure as the monovalent non-aromaticcondensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” asused herein refers to a monovalent group that has two or more condensedrings and includes at least one heteroatom selected from N, O, Si, P,and S, in addition to carbon atoms (e.g., 1 to 60 carbon atoms) asring-forming atoms, wherein the entire molecular structure isnon-aromatic. A non-limiting example of the monovalent non-aromaticcondensed heteropolycyclic group is a carbazolyl group. The term“divalent non-aromatic condensed heteropolycyclic group” as used hereinrefers to a divalent group having substantially the same structure asthe monovalent non-aromatic condensed heteropolycyclic group.

The term “C₅-C₆₀ carbocyclic group” as used herein refers to amonocyclic or polycyclic group having 5 to 60 carbon atoms only asring-forming atoms. The C₅-C₆₀ carbocyclic group may be an aromaticcarbocyclic group or a non-aromatic carbocyclic group. The term “C₅-C₆₀carbocyclic group” as used herein may refer to a ring (e.g., a benzenegroup), a monovalent group (e.g., a phenyl group), or a divalent group(e.g., a phenylene group). Also, depending on the number of substituentsconnected to the C₅-C₆₀ carbocyclic group, the C₅-C₆₀ carbocyclic groupmay be a trivalent group or a quadrivalent group.

The term “C₁-C₆₀ heterocyclic group” as used herein refers to a grouphaving substantially the same structure as the C₅-C₆₀ carbocyclic group,except that at least one heteroatom selected from N, O, Si, P, and S isused as a ring-forming atom, in addition to carbon atoms (e.g., 1 to 60carbon atoms).

In the present specification, at least one substituent of thesubstituted C₅-C₆₀ carbocyclic group, the substituted C₁-C₆₀heterocyclic group, the substituted C₃-C₁₀ cycloalkylene group, thesubstituted C₁-C₁₀ heterocycloalkylene group, the substituted C₃-C₁₀cycloalkenylene group, the substituted C₁-C₁₀ heterocycloalkenylenegroup, the substituted C₆-C₆₀ arylene group, the substituted C₁-C₆₀heteroarylene group, the substituted divalent non-aromatic condensedpolycyclic group, the substituted divalent non-aromatic condensedheteropolycyclic group, the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted C₁-C₆₀ heteroaryloxy group, thesubstituted C₁-C₆₀ heteroarylthio group, the substituted monovalentnon-aromatic condensed polycyclic group, and the substituted monovalentnon-aromatic condensed heteropolycyclic group may be selected from:

deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, anda C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthiogroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthiogroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthiogroup, a monovalent non-aromatic condensed polycyclic group, and amonovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, aC₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂),—B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and —P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

wherein Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, a C₁-C₆₀ alkyl groupsubstituted with at least one selected from deuterium, —F, and a cyanogroup, a C₆-C₆₀ aryl group substituted with at least one selected fromdeuterium, —F, and a cyano group, a biphenyl group, and a terphenylgroup.

The term “Ph” as used herein refers to a phenyl group. The term “Me” asused herein refers to a methyl group. The term “Et” as used hereinrefers to an ethyl group. The term “ter-Bu” or “But” as used hereinrefers to a tert-butyl group. The term “OMe” as used herein refers to amethoxy group.

The term “biphenyl group” as used herein refers to a phenyl groupsubstituted with a phenyl group. For example, a “biphenyl group” may bea substituted phenyl group having a C₆-C₆₀ aryl group as a substituent.

The term “terphenyl group” as used herein refers to a phenyl groupsubstituted with a biphenyl group. For example, a “terphenyl group” maybe a substituted phenyl group having a C₆-C₆₀ aryl group substitutedwith a C₆-C₆₀ aryl group as a substituent.

The symbols * and *′ as used herein, unless defined otherwise, refer toa binding site to an adjacent atom in a corresponding formula.

Hereinafter, compounds and an organic light-emitting device according toembodiments of the present disclosure will be described in more detailwith reference to Synthesis Examples and Examples. The wording “B wasused instead of A” used in describing Synthesis Examples indicates thatan identical number of molar equivalents of B was used in place of A.

EXAMPLES Synthesis Example 1: Synthesis of Compound 1

1) Synthesis of Intermediate 1-A

11.8 grams (g) (50 millimoles (mmol)) of 1,4-dibromobenzene, 3.4 g (50mmol) of pyrazole, 23 g (100 mmol) of tripotassium phosphate, 1.83 g (10mmol) of iodocopper, and 1.17 g (10 mmol) of picolinic acid were addedto a reaction vessel. The mixture was suspended in 100 milliliters (mL)of dimethylsulfoxide. The mixture was stirred at 160° C. for 24 hours.Once the reaction was complete, the mixture was allowed to cool to roomtemperature. Then, 300 mL of distilled water was added thereto, and anorganic layer was extracted using ethyl acetate. The extracted organiclayer was washed with saturated sodium chloride aqueous solution,followed by drying over sodium sulfate. The residue from which thesolvent was removed was separated by column chromatography to therebyobtain 8.9 g (40 mmol) of Intermediate 1-A.

2) Synthesis of Intermediate 1-B

8.9 g (40 mmol) of Intermediate 1-A was suspended in 100 mL oftetrahydrofuran. Then, the suspension was cooled to a temperature of−78° C. 19 mL of n-BuLi (2.5 M in hexane) solution was slowly addeddropwise thereto, followed by stirring at the same temperature for 1hour. Next, 5.0 g (48 mmol) of trimethyl borate was slowly addeddropwise thereto, and the temperature of the mixture was raised to roomtemperature. Then, the mixture was stirred for 12 more hours. Once thereaction was complete, the acidity of the reaction solution was adjustedto pH 5 using 2N HCl solution, followed by stirring for 30 minutes, andan organic layer was extracted using ethyl acetate. The extractedorganic layer was washed with saturated sodium chloride aqueoussolution, followed by drying over sodium sulfate. 6.4 g (34 mmol) ofIntermediate 1-B from which the solvent was removed was obtained.Intermediate 1-B was used in the following reaction without furtherpurification.

3) Synthesis of Intermediate 1-C

6.4 g (34 mmol) of Intermediate 1-B, 5.5 g (17 mmol) of2,2′-dibromodiphenylamine, 4.7 g (34 mmol) of potassium carbonate, and390 mg (0.34 mmol) of tetrakis(phenylphosphine)palladium were added to areaction vessel. The mixture was suspended in a mixture solution of 25mL of tetrahydrofuran and 25 mL of water. The mixture was stirred at120° C. for 24 hours. Once the reaction was complete, the mixture wasallowed to cool to room temperature. Then, 100 mL of distilled water wasadded thereto, and an organic layer was extracted using ethyl acetate.The extracted organic layer was washed with saturated sodium chlorideaqueous solution, followed by drying over sodium sulfate. The residuefrom which the solvent was removed was separated by columnchromatography to thereby obtain 5.0 g (11 mmol) of Intermediate 1-C.

4) Synthesis of Intermediate 1-D

5.0 g (11 mmol) of Intermediate 1-C was suspended in toluene. Thesuspension was cooled to a temperature of −78° C. 4.4 mL of n-BuLi (2.5M in hexane) solution was slowly added dropwise thereto, followed bystirring at 0° C. for 1 hour. Next, 11.0 mL of trichloroboron (1.0 M inhexane) solution was slowly added dropwise thereto, followed by stirringat room temperature for 8 hours. Subsequently, the solvent was removedtherefrom, and a suspension of 5.9 g (44 mmol) of trichloroaluminum, 3.1g (22 mmol) of 2,2,6,6-tetramethyl piperidine, and 70 mL ofo-dichlorobenzene was added dropwise thereto. Then, the mixture wasstirred at a temperature of 160° C. for 12 hours, and 4.9 g (44 mmol) of1,4-diazabicyclo[2.2.2]octane was added dropwise thereto. The solidprecipitate was removed therefrom using a filter. The residue from whichthe solvent was removed was separated by column chromatography tothereby obtain 2.6 g (5.5 mmol) of Intermediate 1-D.

5) Synthesis of Compound 1

2.6 g (5.5 mmol) of Intermediate 1-D, 2.3 g (5.5 mmol) of potassiumtetrachloroplatinate, and 180 mg (0.6 mmol) of tetraammonium bromidewere suspended in 110 mL of acetic acid, followed by stirring at atemperature of 120° C. for 72 hours. Once the reaction was complete, themixture was allowed to cool to room temperature. Then, 100 mL ofdistilled water was added thereto, and a solid compound was filtered.The filtered solid compound was separated by column chromatography tothereby obtain 1.1 g (1.7 mmol) of Compound 1.

Synthesis Example 2: Synthesis of Compound 6

Compound 6 was synthesized in substantially the same manner as inSynthesis Example 1, except that 3,5-dimethyl pyrazole was used insteadof pyrazole.

Synthesis Example 3: Synthesis of Compound 11

1) Synthesis of Intermediate 11-C

11.8 g (50 mmol) of 1,4-dibromobenzene, 6.1 g (50 mmol) of2-pyridineboronic acid, 13.8 g (100 mmol) of potassium carbonate, and1.1 g (1.0 mmol) of tetrakis(phenylphosphine)palladium were added to areaction vessel. The mixture was suspended in a mixture solution of 100mL of tetrahydrofuran and 100 mL of water. The mixture was stirred at120° C. for 24 hours. Once the reaction was complete, the mixture wasallowed to cool to room temperature. Then, 300 mL of distilled water wasadded thereto, and an organic layer was extracted using ethyl acetate.The extracted organic layer was washed with saturated sodium chlorideaqueous solution, followed by drying over sodium sulfate. The residuefrom which the solvent was removed was separated by columnchromatography to thereby obtain 9.8 g (42 mmol) of Intermediate 11-C.

2) Synthesis of Intermediate 11-D

9.8 g (42 mmol) of Intermediate 11-C was suspended in 100 mL oftetrahydrofuran. Then, the suspension was cooled to a temperature of−78° C. 20 mL of n-BuLi (2.5 M in hexane) solution was slowly addeddropwise thereto, followed by stirring at the same temperature for 1hour. Next, 5.2 g (50 mmol) of trimethyl borate was slowly addeddropwise thereto, and the temperature of the mixture was raised to roomtemperature. Then, the mixture was stirred for 12 more hours. Once thereaction was complete, the acidity of the reaction solution was adjustedto pH 5 using 2N HCl solution, followed by stirring for 30 minutes. Oncethe reaction was complete, an organic layer was extracted using ethylacetate. The extracted organic layer was washed with saturated sodiumchloride aqueous solution, followed by drying over sodium sulfate. 6.8 g(34 mmol) of Intermediate 11-D from which the solvent was removed wasobtained. Intermediate 11-D was used in the following reaction withoutfurther purification.

3) Synthesis of Intermediate 11-E

6.4 g (34 mmol) of Intermediate 1-B, 11.0 g (34 mmol) of2,2′-dibromodiphenylamine, 9.4 g (68 mmol) of potassium carbonate, and780 mg (0.68 mmol) of tetrakis(phenylphosphine)palladium were added to areaction vessel. The mixture was suspended in a mixture solution of 50mL of tetrahydrofuran and 50 mL of water. The mixture was stirred at 20°C. for 24 hours. Once the reaction was complete, the mixture was allowedto cool to room temperature. Then, 100 mL of distilled water was addedthereto, and an organic layer was extracted using ethyl acetate. Theextracted organic layer was washed with saturated sodium chlorideaqueous solution, followed by drying over sodium sulfate. The residuefrom which the solvent was removed was separated by columnchromatography to thereby obtain 6.6 g (17 mmol) of Intermediate 11-E.

4) Synthesis of Intermediate 11-F

6.6 g (17 mmol) of Intermediate 11-E, 4.1 g (20.4 mmol) of Intermediate11-D, 4.7 g (34 mmol) of potassium carbonate, and 390 mg (0.34 mmol) oftetrakis(phenylphosphine)palladium were added to a reaction vessel. Themixture was suspended in a mixture solution of 25 mL of tetrahydrofuranand 25 mL of water. The mixture was stirred at 120° C. for 24 hours.Once the reaction was complete, the mixture was allowed to cool to roomtemperature. Then, 100 mL of distilled water was added thereto, and anorganic layer was extracted using ethyl acetate. The extracted organiclayer was washed with saturated sodium chloride aqueous solution,followed by drying over sodium sulfate. The residue from which thesolvent was removed was separated by column chromatography to therebyobtain 5.5 g (11.9 mmol) of Intermediate 11-F.

5) Synthesis of Intermediate 11-G

5.5 g (11.9 mmol) of Intermediate 11-F was suspended in toluene. Thesuspension was cooled to a temperature of −78° C. 4.8 mL of n-BuLi (2.5M in hexane) solution was slowly added dropwise thereto, followed bystirring at 0° C. for 1 hour. Next, 12.0 mL of trichloroboron (1.0 M inhexane) solution was slowly added dropwise thereto, followed by stirringat room temperature for 8 hours. Subsequently, the solvent was removedtherefrom under vacuum, and a suspension of 6.4 g (48 mmol) oftrichloroaluminum, 3.4 g (24 mmol) of 2,2,6,6-tetramethyl piperidine,and 80 mL of o-dichlorobenzene was added dropwise thereto Then, themixture was stirred at a temperature of 160° C. for 12 hours, and 5.3 g(48 mmol) of 1,4-diazabicyclo[2.2.2]octane was added dropwise thereto.The solid precipitate was removed therefrom using a filter. The residuefrom which the solvent was removed was separated by columnchromatography to thereby obtain 2.4 g (5.1 mmol) of Intermediate 11-G.

6) Synthesis of Compound 11

2.4 g (5.1 mmol) of Intermediate 11-G, 2.1 g (5.1 mmol) of potassiumtetrachloroplatinate, and 160 mg (0.5 mmol) of tetraammonium bromidewere suspended in 100 mL of acetic acid, followed by stirring at atemperature of 120° C. for 72 hours. Once the reaction was complete, themixture was allowed to cool to room temperature. Then, 100 mL ofdistilled water was added thereto, and a solid compound was filtered.The filtered solid compound was separated by column chromatography tothereby obtain 850 mg (1.3 mmol) of Compound 11.

Synthesis Example 4: Synthesis of Compound 16

780 mg (1.1 mmol) of Compound 16 was obtained in substantially the samemanner as in Synthesis Example 3, except that Intermediate 6-B was usedinstead of Intermediate 1-B, and 4-methylpyridine-2-boronic acid wasused instead of 2-pyridineboronic acid.

Synthesis Example 5: Synthesis of Compound 21

1) Synthesis of Intermediate 21-C

11.8 g (50 mmol) of 1,4-dibromobenzene, 5.9 g (50 mmol) ofbenzimidazole, 23 g (100 mmol) of tripotassium phosphate, 1.83 g (10mmol) of iodocopper, and 1.17 g (10 mmol) of picolinic acid were addedto a reaction vessel. The mixture was suspended in 100 mL ofdimethylsulfoxide. The mixture was stirred at 160° C. for 24 hours. Oncethe reaction was complete, the mixture was allowed to cool to roomtemperature. Then, 300 mL of distilled water was added thereto, and anorganic layer was extracted using ethyl acetate. The extracted organiclayer was washed with saturated sodium chloride aqueous solution,followed by drying over sodium sulfate. The residue from which thesolvent was removed was separated by column chromatography to therebyobtain 9.6 g (35 mmol) of Intermediate 21-C.

2) Synthesis of Intermediate 21-D

9.6 g (35 mmol) of Intermediate 21-C was suspended in 100 mL oftetrahydrofuran. Then, the suspension was cooled to a temperature of−78° C. 19 mL of n-BuLi (2.5 M in hexane) solution was slowly addeddropwise thereto, followed by stirring at the same temperature for 1hour. Next, 4.3 g (42 mmol) of trimethyl borate was slowly addeddropwise thereto, and the temperature of the mixture was raised to roomtemperature. Then, the mixture was stirred for 12 more hours. Once thereaction was complete, the acidity of the reaction solution was adjustedto pH 5 using 2N HCl solution, followed by stirring for 30 minutes. Oncethe reaction was complete, an organic layer was extracted using ethylacetate. The extracted organic layer was washed with saturated sodiumchloride aqueous solution, followed by drying over sodium sulfate. Thesolvent was removed to obtain 7.2 g (30 mmol) of Intermediate 21-C.Intermediate 21-C was used in the following reaction without any furtherpurification.

3) Synthesis of Intermediate 21-F

6.6 g (17 mmol) of Intermediate 11-E, 4.9 g (20.4 mmol) of Intermediate21-D, 4.7 g (34 mmol) of potassium carbonate, and 390 mg (0.34 mmol) oftetrakis(phenylphosphine)palladium were added to a reaction vessel. Themixture was suspended in a mixture solution of 25 mL of tetrahydrofuranand 25 mL of water. The mixture was stirred at 120° C. for 24 hours.Once the reaction was complete, the mixture was allowed to cool to roomtemperature. Then, 100 mL of distilled water was added thereto, and anorganic layer was extracted using ethyl acetate. The extracted organiclayer was washed with saturated sodium chloride aqueous solution,followed by drying over sodium sulfate. The residue from which thesolvent was removed was separated by column chromatography to therebyobtain 5.6 g (11.1 mmol) of Intermediate 21-F.

4) Synthesis of Intermediate 21-G

5.6 g (11.1 mmol) of Intermediate 21-F was suspended in toluene. Thesuspension was cooled to a temperature of −78° C. 5 mL of n-BuLi (2.5 Min hexane) solution was slowly added dropwise thereto, followed bystirring at 0° C. for 1 hour. Next, 11.2 mL of trichloroboron (1.0 M inhexane) solution was slowly added dropwise thereto, followed by stirringat room temperature for 8 hours. Subsequently, the solvent was removedtherefrom under vacuum, and a suspension of 6.0 g (45 mmol) oftrichloroaluminum, 3.2 g (22 mmol) of 2,2,6,6-tetramethyl piperidine,and 75 mL of o-dichlorobenzene was added dropwise thereto Then, themixture was stirred at a temperature of 160° C. for 12 hours, and 4.9 g(45 mmol) of 1,4-diazabicyclo[2.2.2]octane was added dropwise thereto.The solid precipitate was removed therefrom using a filter. The residuefrom which the solvent was removed was separated by columnchromatography to thereby obtain 2.6 g (5.0 mmol) of Intermediate 21-G.

5) Synthesis of Intermediate 21-H

5.6 g (11.1 mmol) of Intermediate 21-G and 3.2 g (22.2 mmol) of iodizedmethyl were suspended in 110 mL of toluene, followed by stirring at atemperature of 110° C. for 12 hours. Once the reaction was complete, themixture was cooled to room temperature. Then, the solid compound wasfiltered and washed using ethyl ether. The result was then dried toobtain 6.9 g (10.5 mmol) of Intermediate 21-H.

6) Synthesis of Intermediate 21-1

6.9 g (10.5 mmol) of Intermediate 21-H was suspended in a mixturesolution of 55 mL of methyl alcohol and 55 mL of water. Subsequently,2.6 g (15.8 mmol) of ammonium hexafluorophosphate was added dropwisethereto, followed by stirring at room temperature for 12 hours. Once thereaction was complete, the solid compound was filtered and washed usingethyl ether. The result was then dried to obtain 6.3 g (9.5 mmol) ofIntermediate 21-1.

7) Synthesis of Compound 21

6.3 g (9.5 mmol) of Intermediate 21-1, 3.9 g (10.5 mmol) ofdichloro(1,5-cyclooctadiene)platinum, and 1.6 g (19.0 mmol) of sodiumacetate were suspended in 100 mL of dioxane. The mixture was stirred at110° C. for 24 hours. Once the reaction was complete, the mixture wasallowed to cool to room temperature. Then, 200 mL of distilled water wasadded thereto, and an organic layer was extracted using ethyl acetate.The extracted organic layer was washed with saturated sodium chlorideaqueous solution, followed by drying over sodium sulfate. The residuefrom which the solvent was removed was separated by columnchromatography to thereby obtain 2.2 g (3.1 mmol) of Compound 21.

Synthesis Example 6: Synthesis of Compound 26

1.9 g (2.5 mmol) of Compound 26 was obtained in substantially the samemanner as in Synthesis Example 5, except that Intermediate 16-E was usedinstead of Intermediate 11-E.

Synthesis Example 7: Synthesis of Compound 31

1) Synthesis of Intermediate 31-C

11.8 g (50 mmol) of 1,4-dibromobenzene, 3.5 g (50 mmol) of1H-1,2,3-triazole, 23 g (100 mmol) of tripotassium phosphate, 1.83 g (10mmol) of iodocopper, and 1.17 g (10 mmol) of picolinic acid were addedto a reaction vessel. The mixture was suspended in 100 mL ofdimethylsulfoxide. The mixture was stirred at 160° C. for 24 hours. Oncethe reaction was complete, the mixture was allowed to cool to roomtemperature. Then, 300 mL of distilled water was added thereto, and anorganic layer was extracted using ethyl acetate. The extracted organiclayer was washed with saturated sodium chloride aqueous solution,followed by drying over sodium sulfate. The residue from which thesolvent was removed was separated by column chromatography to therebyobtain 8.7 g (39 mmol) of Intermediate 31-C.

2) Synthesis of Intermediate 31-D

8.7 g (39 mmol) of Intermediate 31-C was suspended in 100 mL oftetrahydrofuran. Then, the suspension was cooled to a temperature of−78° C. 19 mL of n-BuLi (2.5 M in hexane) solution was slowly addeddropwise thereto, followed by stirring at the same temperature for 1hour. Next, 4.8 g (48 mmol) of trimethyl borate was slowly addeddropwise thereto, and the temperature of the mixture was raised to roomtemperature. Then, the mixture was stirred for 12 more hours. Once thereaction was complete, the acidity of the reaction solution was adjustedto pH 5 using 2N HCl solution, followed by stirring for 30 minutes. Oncethe reaction was complete, an organic layer was extracted using ethylacetate. The extracted organic layer was washed with saturated sodiumchloride aqueous solution, followed by drying over sodium sulfate. Thesolvent was removed to obtain 6.2 g (33 mmol) of Intermediate 31-D.Intermediate 31-D was used in the following reaction without furtherpurification.

3) Synthesis of Intermediate 31-F

6.6 g (17 mmol) of Intermediate 11-E, 3.9 g (20.4 mmol) of Intermediate31-D, 4.7 g (34 mmol) of potassium carbonate, and 390 mg (0.34 mmol) oftetrakis(phenylphosphine)palladium were added to a reaction vessel. Themixture was suspended in a mixture solution of 25 mL of tetrahydrofuranand 25 mL of water. The mixture was stirred at 120° C. for 24 hours.Once the reaction was complete, the mixture was allowed to cool to roomtemperature. Then, 100 mL of distilled water was added thereto, and anorganic layer was extracted using ethyl acetate. The extracted organiclayer was washed with saturated sodium chloride aqueous solution,followed by drying over sodium sulfate. The residue from which thesolvent was removed was separated by column chromatography to therebyobtain 5.3 g (11.6 mmol) of Intermediate 31-F.

4) Synthesis of Intermediate 31-G

5.3 g (11.6 mmol) of Intermediate 31-F was suspended in toluene. Thesuspension was cooled to a temperature of −78° C. 4.7 mL of n-BuLi (2.5M in hexane) solution was slowly added dropwise thereto, followed bystirring at 0° C. for 1 hour. Next, 11.7 mL of trichloroboron (1.0 M inhexane) solution was slowly added dropwise thereto, followed by stirringat room temperature for 8 hours. Subsequently, the solvent was removedtherefrom under vacuum, and a suspension of 6.3 g (48 mmol) oftrichloroaluminum, 3.5 g (24 mmol) of 2,2,6,6-tetramethyl piperidine,and 80 mL of o-dichlorobenzene was added dropwise thereto Then, themixture was stirred at a temperature of 160° C. for 12 hours, and 5.3 g(48 mmol) of 1,4-diazabicyclo[2.2.2]octane was added dropwise thereto.The solid precipitate was removed therefrom using a filter. The residuefrom which the solvent was removed was separated by columnchromatography to thereby obtain 2.1 g (4.6 mmol) of Intermediate 31-G.

5) Synthesis of Compound 31

2.1 g (4.6 mmol) of Intermediate 31-G, 1.9 g (4.6 mmol) of potassiumtetrachloroplatinate, and 160 mg (0.5 mmol) of tetraammonium bromidewere suspended in 100 mL of acetic acid, followed by stirring at atemperature of 120° C. for 72 hours. Once the reaction was complete, themixture was allowed to cool to room temperature. Then, 100 mL ofdistilled water was added thereto, and a solid compound was filtered.The filtered solid compound was separated by column chromatography tothereby obtain 740 mg (1.1 mmol) of Compound 31.

Synthesis Example 8: Synthesis of Compound 36

1.0 g (1.6 mmol) of Compound 36 was obtained in substantially the samemanner as in Synthesis Example 7, except that 2H-1,2,3-triazole was usedinstead of ¹H-1,2,3-triazole.

The compounds synthesized in Synthesis Examples 1 to 8 were identifiedby ¹H nuclear magnetic resonance (NMR) and mass spectroscopy/fast atombombardment (MS/FAB). The results thereof are shown in Table 1.

Methods of synthesizing compounds other than the compounds shown inTable 1 may be easily understood by those skilled in the art byreferring to the synthesis pathways and raw materials described above.

TABLE 1 MS/FAB Compound ¹H NMR (CDCl₃, 400 MHz) found calc. 1 8.46-8.08(6H, m), 7.81-7.48 (4H, m), 654.1301 654.1303 7.38-7.31 (4H, m),7.13-7.05 (2H, m), 6.88-6.75 (2H, m) 6 8.08-7.91 (2H, m), 7.81-7.44 (4H,m), 710.1924 710.1929 7.37-7.29 (4H, m), 7.14-7.10 (2H, m), 6.40 (2H,s), 2.90 (6H, s), 2.80 (6H, s) 11 8.56-8.45 (2H, m), 8.35-8.30 (2H, m),655.1348 665.1351 8.11-7.95 (3H, m), 7.82-7.75 (3H, m), 7.38-7.25 (5H,m), 7.15-7.10 (2H, m), 7.01-6.79 (2H, m) 16 8.57-8.33 (2H, m), 8.09-7.95(3H, m), 707.1815 707.1820 7.80-7.71 (3H, m), 7.39-7.31 (4H, m),7.15-7.04 (3H, m), 6.40 (3H, s), 2.91 (3H, s), 2.74 (3H, s), 2.45 (3H,s) 21 8.56-8.55 (1H, m), 8.10-8.08 (2H, m), 718.1612 718.1616 7.87-7.70(5H, m), 7.64-7-14 (10H, m), 6.50-6.46 (1H, m), 3.88 (3H, s) 268.57-8.54 (1H, m), 8.13-8.06 (2H, m), 746.1922 746.1929 7.89-7.71 (5H,m), 7.64-7-14 (8H, m), 6.50-6.46 (1H, m), 3.89 (3H, s), 2.21 (3H, s),1.95 (3H, s) 31 8.64-8.35 (4H, m), 8.15-8.09 (2H, m), 655.1251 655.12557.81-7.75 (4H, m), 7.38-7.29 (4H, m), 7.15-7.09 (2H, m), 6.88-6.85 (1H,m) 36 8.49-8.33 (4H, m), 8.09-8.05 (2H, m), 655.1250 655.1255 7.80-7.76(4H, m), 7.38-7.29 (4H, m), 7.13-7.11 (2H, m), 6.87-6.81 (1H, m)

Example 1

As an anode, an ITO glass substrate (having a thickness of 1,200 Å,available from Corning Co., Ltd) was cut to a size of 50 millimeters(mm)×50 mm×0.7 mm, sonicated in isopropyl alcohol and pure water for 5minutes in each solvent, cleaned with ultraviolet rays for 30 minutes,and then ozone, and mounted on a vacuum deposition apparatus.

2-TNATA was vacuum-deposited on the ITO substrate to form a holeinjection layer having a thickness of 600 Å. NPB was vacuum-deposited onthe hole injection layer to form a hole transport layer having athickness of 300 Å.

BCPDS, POPCPA, and Compound 1 were co-deposited at a ratio of 45:45:10on the hole transport layer to form an emission layer having a thicknessof 300 Å.

Subsequently, TSPO1 was vacuum-deposited on the emission layer to form ahole blocking layer having a thickness of 50 Å. Alq₃ wasvacuum-deposited on the hole blocking layer to form an electrontransport layer having a thickness of 300 Å. LiF was deposited on theelectron transport layer to form an electron injection layer having athickness of 10 Å. Al was vacuum-deposited on the electron injectionlayer to form a cathode having a thickness of 3,000 Å, therebycompleting the manufacture of an organic light-emitting device.

Examples 2 to 8 and Comparative Examples 1 to 3

Additional organic light-emitting devices were manufactured insubstantially the same manner as in Example 1, except that the compoundsshown in Table 2 were used instead of Compound 1 in the formation of anemission layer.

Evaluation Example

The driving voltage, current density, luminance, emission color, andemission wavelengths of the organic light-emitting devices manufacturedin Examples 1 to 8 and Comparative Examples 1 to 3 were measured using aKeithley SMU 236 and a luminance meter PR650 at a current density of 50mA/cm². The results thereof are shown in Table 2.

TABLE 2 Driv- Cur- Cur- Emis- ing rent Lu- rent sion Emis- vol- densitymin- effi- Emis- wave- sion tage (mA/ ance ciency sion length layer (V)cm²) (cd/m²) (cd/A) color (nm) Example 1  1 5.35 50 4130 8.25 Blue 466Example 2  6 5.29 51 4230 8.31 Blue 460 Example 3 11 5.41 55 4002 8.05Blue 475 Example 4 16 5.43 56 4113 8.12 Blue 473 Example 5 21 5.41 494222 8.29 Blue 480 Example 6 26 5.39 52 4321 8.44 Blue 477 Example 7 315.66 49 4109 8.25 Blue 470 Example 8 36 5.74 47 3988 8.01 Blue 471 Com-A 6.56 50 3870 7.74 Blue 478 parative Example 1 Com- B 5.99 49 3850 7.65Blue 490 parative Example 2 Com- C 6.30 48 3650 7.44 Blue 495 parativeExample 3

Referring to the results of Table 2, it was found that the organiclight-emitting devices manufactured in Examples 1 to 8 had improveddriving voltage, improved luminance, and improved current efficiency,compared with the organic light-emitting devices manufactured inComparative Examples 1 to 3.

As is apparent from the foregoing description, an organic light-emittingdevice including the organometallic compound may have a low drivingvoltage, excellent luminance, and a high current efficiency.

As used herein, the terms “use”, “using”, and “used” may be consideredsynonymous with the terms “utilize”, “utilizing”, and “utilized”,respectively. Further, the use of “may” when describing embodiments ofthe present disclosure refers to “one or more embodiments of the presentdisclosure”.

As used herein, the terms “substantially”, “about”, and similar termsare used as terms of approximation and not as terms of degree, and areintended to account for the inherent deviations in measured orcalculated values that would be recognized by those of ordinary skill inthe art.

Also, any numerical range recited herein is intended to include allsubranges of the same numerical precision subsumed within the recitedrange. For example, a range of “1.0 to 10.0” is intended to include allsubranges between (and including) the recited minimum value of 1.0 andthe recited maximum value of 10.0, that is, having a minimum value equalto or greater than 1.0 and a maximum value equal to or less than 10.0,such as, for example, 2.4 to 7.6. Any maximum numerical limitationrecited herein is intended to include all lower numerical limitationssubsumed therein and any minimum numerical limitation recited in thisspecification is intended to include all higher numerical limitationssubsumed therein. Accordingly, Applicant reserves the right to amendthis specification, including the claims, to expressly recite anysub-range subsumed within the ranges expressly recited herein.

It should be understood that the embodiments described herein should beconsidered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as being available for other similarfeatures or aspects in other embodiments.

While one or more embodiments have been described with reference to thedrawings, it will be understood by those of ordinary skill in the artthat various changes in form and details may be made therein withoutdeparting from the spirit and scope of the disclosure, as defined by thefollowing claims and equivalents thereof.

What is claimed is:
 1. An organometallic compound represented by Formula1:

wherein, in Formulae 1 and 1-1, M₁ is selected from a first-rowtransition metal, a second-row transition metal, and a third-rowtransition metal, L₁ is a ligand represented by Formula 1-1, L₂ isselected from a monodentate ligand and a bidentate ligand, n1 is 1, n2is selected from 0, 1, and 2, A₁₁ to A₁₆ are each independently selectedfrom a C₅-C₆₀ carbocyclic group and a C₁-C₆₀ heterocyclic group, X₁₁ toX₁₈ are each independently selected from nitrogen (N) and carbon (C),Y₁₁ to Y₁₄ are each independently selected from N, C, oxygen (O), andsulfur (S), i) Z₁₁ is boron (B), and Z₁₂ is N; or ii) Z₁₁ is N, and Z₁₂is B, T₁₁ to T₁₄ are each independently selected from a single bond,*—O—*′, *—S—*′, *—N(R₁₇)—*′, and *—C(R₁₇)(R₁₈)—*′, L₁₁ to L₁₃ are eachindependently selected from a single bond, *—O—*′, *—S—*′,*—C(R₁₉)(R₂₀)—*′, *—C(R₁₉)═*′, *═C(R₁₉)—*′, *—C(R₁₉)═C(R₂₀)—*′,*—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R₁₉)—*′, *—N(R₁₉)—*′, *—P(R₁₉)—*′,*—Si(R₁₉)(R₂₀)—*′, *—P(R₁₉)(R₂₀)—*′, and *—Ge(R₁₉)(R₂₀)—*′, a11 to a13are each independently selected from 0, 1, 2, and 3, provided that atleast two selected from a11 to a13 are selected from 1, 2, and 3, whena11 is 0, A₁₁ and A₁₃ are not linked to each other, when al 2 is 0, A₁₂and A₁₄ are not linked to each other, when a13 is 0, A₁₁ and A₁₂ are notlinked to each other, R₁₁ to R₂₀ are each independently selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryloxy group, a substituted or unsubstitutedC₁-C₆₀ heteroarylthio group, a substituted or unsubstituted monovalentnon-aromatic condensed polycyclic group, a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —N(Q₁)(Q₂), —P(Q₁)(Q₂), —C(═O)(Q₁),—S(═O)(Q₁), —S(═O)₂(Q₁), —P(═O)(Q₁)(Q₂), and —P(═S)(Q₁)(Q₂), at leasttwo adjacent groups selected from R₁₁ to R₂₀ are optionally bound toform a substituted or unsubstituted C₅-C₆₀ carbocyclic group or asubstituted or unsubstituted C₁-C₆₀ heterocyclic group, b11 to b16 areeach independently selected from 1, 2, 3, 4, 5, 6, 7, and 8, wherein Q₁to Q₃ are each independently selected from hydrogen, deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthiogroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group, 1 to *4 each independently indicate abinding site to M₁, and and *′ each indicate a binding site to anadjacent atom.
 2. The organometallic compound of claim 1, wherein M₁ isselected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag),gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os),titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium(Tb), and thulium (Tm).
 3. The organometallic compound of claim 1,wherein A₁₁ and A₁₂ are each independently selected from a C₅-C₆₀carbocyclic group and a C₁-C₆₀ heterocyclic group, and A₁₃ to A₁₆ areeach independently selected from a C₅-C₆₀ carbocyclic group.
 4. Theorganometallic compound of claim 1, wherein A₁₁ to A₁₆ are eachindependently selected from a benzene group, a naphthalene group, ananthracene group, a phenanthrene group, a phenalene group, atriphenylene group, a pyrene group, a chrysene group, a cyclopentadienegroup, a tetrahydronaphthalene group, a furan group, a thiophene group,a silole group, an indene group, a fluorene group, an indole group, acarbazole group, a benzofuran group, a dibenzofuran group, abenzothiophene group, a dibenzothiophene group, a benzosilole group, adibenzosilole group, an indenopyridine group, an indolopyridine group, abenzofuropyridine group, a benzothienopyridine group, abenzosilolopyridine group, an indenopyrimidine group, anindolopyrimidine group, a benzofuropyrimidine group, abenzothienopyrimidine group, a benzosilolopyrimidine group, adihydropyridine group, a pyridine group, a pyrimidine group, a pyrazinegroup, a pyridazine group, a triazine group, a quinoline group, anisoquinoline group, a quinoxaline group, a quinazoline group, aphenanthroline group, a benzoquinoline group, a benzoisoquinoline group,a benzoquinoxaline group, a benzoquinazoline group, a pyrrole group, apyrazole group, an imidazole group, a dihydroimidazole group, a triazolegroup, a dihydrotriazole group, an oxazole group, an iso-oxazole group,a thiazole group, an isothiazole group, an oxadiazole group, athiadiazole group, a benzopyrazole group, a benzimidazole group, adihydrobenzimidazole group, an imidazopyridine group, adihydroimidazopyridine group, an imidazopyrimidine group, adihydroimidazopyrimidine group, an imidazopyrazine group, adihydroimidazopyrazine group, a benzoxazole group, a benzothiazolegroup, a benzoxadiazole group, a benzothiadiazole group, atetrahydroisoquinoline group, and a tetrahydroquinoline group.
 5. Theorganometallic compound of claim 1, wherein: A₁₁ and A₁₂ are eachindependently selected from an indole group, a carbazole group, apyridine group, a pyrimidine group, a pyrazine group, a pyridazinegroup, a triazine group, a quinoline group, an isoquinoline group, aquinoxaline group, a quinazoline group, a pyrazole group, an imidazolegroup, a dihydroimidazole group, a triazole group, a dihydrotriazolegroup, an oxazole group, an iso-oxazole group, a thiazole group, anisothiazole group, an oxadiazole group, a thiadiazole group, abenzopyrazole group, a benzimidazole group, a dihydrobenzimidazolegroup, a dihydroimidazopyridine group, a dihydroimidazopyrimidine group,a dihydroimidazopyrazine group, a benzoxazole group, and a benzothiazolegroup, and A₁₃ to A₁₆ are each independently selected from a benzenegroup, a naphthalene group, an indene group, a fluorene group, abenzofuran group, a dibenzofuran group, a benzothiophene group, and adibenzothiophene group.
 6. The organometallic compound of claim 1,wherein A₁₃ to A₁₆ are each independently a benzene group.
 7. Theorganometallic compound of claim 1, wherein X₁₁ to X₁₈ are each C. 8.The organometallic compound of claim 1, wherein Y₁₁ to Y₁₄ are eachindependently selected from N and C.
 9. The organometallic compound ofclaim 1, wherein T₁₁ to T₁₄ are each a single bond.
 10. Theorganometallic compound of claim 1, wherein a11 and a12 are eachselected from 1, 2, and 3, and al 3 is 0 or
 1. 11. The organometalliccompound of claim 1, wherein R₁₁ to R₂₀ are each independently selectedfrom: hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C₁-C₂₀alkyl group, and a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group and aC₁-C₂₀ alkoxy group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a cyano group, a phenyl group, a biphenylgroup, and a terphenyl group; a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a biphenyl group, a terphenyl group, a pentalenyl group, anindenyl group, a naphthyl group, an azulenyl group, an indacenyl group,an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenylgroup, a pentacenyl group, a pyrrolyl group, a thiophenyl group, afuranyl group, a silolyl group, an imidazolyl group, a pyrazolyl group,a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an indolyl group, an isoindolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a benzoisoquinolinyl group, aphthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, abenzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinylgroup, a cinnolinyl group, a phenanthridinyl group, an acridinyl group,a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, a benzosilolyl group, abenzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, abenzoisoxazolyl group, a triazolyl group, a tetrazolyl group, athiadiazolyl group, an oxadiazolyl group, a triazinyl group, acarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, adibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranylgroup, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, adibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenylgroup, a dinaphthosilolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinylgroup, a benzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, anindenopyrrolyl group, an indolopyrrolyl group, an indenocarbazolylgroup, and an indolocarbazolyl group; a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, an indacenylgroup, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenylgroup, a furanyl group, a silolyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a benzoquinoxalinyl group, a quinazolinyl group, abenzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, abenzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, abenzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, abenzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, atetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, atriazinyl group, a carbazolyl group, a dibenzofuranyl group, adibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolylgroup, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, anaphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranylgroup, a dinaphthothiophenyl group, a dinaphthosilolyl group, animidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinylgroup, a thiazolopyridinyl group, a benzonaphthyridinyl group, anazafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolylgroup, an azadibenzofuranyl group, an azadibenzothiophenyl group, anazadibenzosilolyl group, an indenopyrrolyl group, an indolopyrrolylgroup, an indenocarbazolyl group, and an indolocarbazolyl group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a cyano group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a pentalenyl group, an indenyl group, anaphthyl group, an azulenyl group, an indacenyl group, an acenaphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenylgroup, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenylgroup, an anthracenyl group, a fluoranthenyl group, a triphenylenylgroup, a pyrenyl group, a chrysenyl group, a perylenyl group, apentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group,a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolylgroup, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, an indolyl group, an isoindolyl group, an indazolyl group, apurinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group,a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group,a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, abenzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group,a triazolyl group, a tetrazolyl group, a thiadiazolyl group, anoxadiazolyl group, a triazinyl group, a carbazolyl group, adibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group,a benzocarbazolyl group, a naphthobenzofuranyl group, anaphthobenzothiophenyl group, a naphthobenzosilolyl group, adibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenylgroup, a dinaphthosilolyl group, an imidazopyridinyl group, animidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinylgroup, a benzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, anindenopyrrolyl group, an indolopyrrolyl group, an indenocarbazolylgroup, an indolocarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁) (Q₃₂), —C(═O)(Q₃₁), —S(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂),and —P(═S)(Q₃₁)(Q₃₂); and —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂),—C(═O)(Q₁), —S(═O)(Q₁), —S(═O)₂(Q₁), —P(═O)(Q₁)(Q₂), and —P(═S)(Q₁)(Q₂),wherein Q₁ to Q₃ and Q₃₁ to Q₃₃ are each independently selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.
 12. The organometallic compound of claim1, wherein L₁ is represented by one selected from Formulae 1-11 and1-12:

wherein, in Formulae 1-11 and 1-12, 1 to *4, A₁₁ to A₁₆, Y₁₁ to Y₁₄,L₁₁, L₁₂, a11, a12, R₁₁ to R₁₆, and b11 to b16 are each the same as inFormula 1-1.
 13. The organometallic compound of claim 1, wherein L₁ isrepresented by one selected from Formulae 1-31 and 1-32:

wherein, in Formulae 1-31 and 1-32, 1 to *4, A₁₁, A₁₂, Y₁₃, Y₁₄, L₁₁,L₁₂, a11, a12, R₁₁, R₁₂, and b11 to b16 are each the same as in Formula1-1, and R_(13a), R_(13b), R_(14a), R_(14b), R_(15a) to R_(15d), andR_(16a) to R_(16d) are each the same as R₁₃ in Formula 1-1.
 14. Theorganometallic compound of claim 1, wherein L₂ is represented by oneselected from Formulae 7-1 to 7-11:

wherein, in Formulae 7-1 to 7-11, A₇₁ and A₇₂ are each independentlyselected from a C₅-C₂₀ carbocyclic group and a C₁-C₂₀ heterocyclicgroup, X₇₁ and X₇₂ are each independently selected from C and N, X₇₃ isN or C(Q₇₃), X₇₄ is N or C(Q₇₄), X₇₅ is N or C(Q₇₅), X₇₆ is N or C(Q₇₆),and X₇₇ is N or C(Q₇₇), X₇₈ is O, S, or N(Q₇₈), and X₇₉ is O, S, orN(Q₇₉), Y₇₁ and Y₇₂ are each independently selected from a single bond,a double bond, a substituted or unsubstituted C₁-C₅ alkylene group, asubstituted or unsubstituted C₂-C₅ alkenylene group, and a substitutedor unsubstituted C₆-C₁₀ arylene group, Z₇₁ and Z₇₂ are eachindependently selected from N, O, N(R₇₅), P(R₇₅)(R₇₆), and As(R₇₅)(R₇₆),Z₇₃ is selected from phosphorus (P) and arsenic (As), Z₇₄ is selectedfrom CO and C(R₇₅)(R₇₆), R₇₁ to R₈₀ and Q₇₃ to Q₇₉ are eachindependently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, wherein R₇₁ and R₇₂ areoptionally bound to form a ring, R₇₇ and R₇₈ are optionally bound toform a ring, R₇₈ and R₇₉ are optionally bound to form a ring, and R₇₉and R₈₀ are optionally bound to form a ring, b71 and b72 are eachindependently selected from 1, 2, and 3, and and *′ each indicate abinding site to an adjacent atom.
 15. The organometallic compound ofclaim 1, wherein M₁ is selected from Pt and Pd, n1 is 1, and n2 is 0.16. The organometallic compound of claim 1, wherein the organometalliccompound represented by Formula 1 is selected from Compounds 1 to 240:

wherein in Compounds 1 to 240, “Ph” represents a phenyl group.
 17. Theorganometallic compound of claim 1, wherein the organometallic compoundis to emit blue light having a maximum emission wavelength of about 450nanometers (nm) or greater and less than about 490 nm.
 18. An organiclight-emitting device comprising: a first electrode; a second electrode;and an organic layer between the first electrode and the secondelectrode and comprising an emission layer, wherein the organic layercomprises the organometallic compound of claim
 1. 19. The organiclight-emitting device of claim 18, wherein: the first electrode is ananode, the second electrode is a cathode, the organic layer comprises ahole transport region between the first electrode and the emission layerand/or an electron transport region between the emission layer and thesecond electrode, wherein the hole transport region comprises a holeinjection layer, a hole transport layer, an emission auxiliary layer, anelectron blocking layer, or a combination thereof, and the electrontransport region comprises a hole blocking layer, an electron transportlayer, an electron injection layer, or a combination thereof.
 20. Theorganic light-emitting device of claim 18, wherein the emission layercomprises the organometallic compound.